Novel polyesteramides, processes for the preparation thereof, and polyesteramide compositions

ABSTRACT

The present application discloses novel polyesteramides comprising cycloalkyl diols and/or cycloalkyl dialkanols with tunable properties based on the monomers and monomerratios used to prepare the polyesteramides and varying the reaction conditions. The present application also discloses compositions and articles.

BACKGROUND OF THE INVENTION

Thermoplastic polymers are useful in a wide variety of applications,including, for example, various electrical, automotive, medical,consumer, industrial, and packaging applications. Thermoplastic polymersare advantaged over thermoset plastics in that thermoplastic polymerscan be easily melt processed into a variety of useful articles.

Different types of thermoplastic polymers have different properties thatmake them desirable for certain end uses. Elastomeric thermoplasticpolymers generally have glass transition temperature values below roomtemperature and low modulus values making them suitable for applicationsrequiring flexibility and stretchability. In contrast, rigidthermoplastic polymers generally have glass transition temperaturevalues above room temperature and high modulus values making themsuitable for applications requiring stiffness and strength.

Polyesteramides are one class of thermoplastic polymers which are formedfrom the polycondensation of diacids, diols, and diamines (e.g.,WO2008112833, U.S. Pat. Nos. 5,672,676, 2,281,415, CA2317747).Polyesteramides have attracted strong industrial interest primarilybecause of their excellent heat resistance properties (U.S. Pat. No.5,672,676), their amenability to processing and their potential forbiodegradability. (e.g., WO2008112833)

The present application discloses novel polyesteramides comprising TMCDand/or CHDM having tunable properties by adjusting the monomer ratiosand varying the reaction conditions. The polyesteramides are useful in avariety of engineering plastics applications wherein chemicalresistance, UV resistance, moisture barrier, surface energy, heatresistance, mechanical, optical, and/or melt processibility propertiesare important.

SUMMARY OF THE INVENTION

The present application discloses a polyesteramide comprising:

-   -   (a) a diamine component comprising:        -   1 to 99 mole % of diamine residues derived from diamine            chosen from CH₂((C₃₋₈)cycloalkyl-NH₂)₂;    -   (b) a diol component comprising:        -   1 to 99 mole % of diol residues derived from a diol chosen            from (C₃₋₈)cycloalkyl di((C₁₋₃)alkanol); and    -   (c) a diacid component comprising:        -   10 to 100 mole % of diacid residues derived from a diacid            chosen from HO₂C—(C₂₋₄₀)alkylene-CO₂H, or            HO₂C—(C₃₋₁₀)cycloalkyl-CO₂H;    -   wherein each cycloalkyl is unsubstituted or substituted by 1-4        (C₁₋₃)alkyl,    -   wherein the total mole % of the diacid component is 100 mole %,        and    -   wherein the total mole % of the combined diol and diamine        component is 100 mole %.    -   The present application also discloses compositions and articles        comprising the polyesteramides and processes for making the        polyesteramides.

DETAILED DESCRIPTION OF THE INVENTION

In this specification and in the claims that follow, reference will bemade to a number of terms, which shall be defined to have the followingmeanings.

The singular forms “a,” “an,” and “the” include plural referents unlessthe context clearly dictates otherwise.

“Diol” means a chemical with two alcohol functional groups. Examplesinclude 1,4-butanediol, propylene glycol,2,2,4,4-tetramethyl-1,3-cyclobutanediol, 1,4-cyclohexanedimethanol,propylene-1,3-diol, and the like.

“Diamine” means a chemical with two amino functional groups. Examplesinclude 1,6-diaminohexane, ethylenediamine,4,4′-methylenebis(2-methylcyclohexylamine),5-amino-1,3,3-trimethylcyclohexanemethylamine,4,4′-methylenebis(cyclohexylamine), 1,4-bis(aminomethyl)cyclohexane andthe like.

“Alkanol” means an alkane or alkyl group comprising an alcohol group.Examples include methanol, ethanol, propanol, butyl alcohol, and thelike.

“Diacid” means a chemical with two carboxylic acid groups. Examplesinclude 1,12-dodecanedioic acid, adipic acid, Cyclohexanedicarboxylicand the like.

Values may be expressed as “about” or “approximately” a given number.Similarly, ranges may be expressed herein as from “about” one particularvalue and/or to “about” or another particular value. When such a rangeis expressed, another aspect includes from the one particular valueand/or to the other particular value. Similarly, when values areexpressed as approximations, by use of the antecedent “about,” it willbe understood that the particular value forms another aspect.

As used herein the term “chosen from” when used with “and” or “or” havethe following meanings: For example, a variable chosen from A, B and Cmeans that the variable can be A alone, B alone, or C alone. Forexample, a variable A, B, or C means that the variable can be A alone, Balone, C alone, A and B in combination, B and C, A and C in combination,or A, B, and C in combination.

As used herein, the term “residue(s)” refers to the monomer unit orrepeating unit in a polymer, oligomer or dimer. For example, a polymercan be made from the condensation of the following monomers:terephthalic acid (“TPA”) and cyclohexyl-1,4-dimethanol (“CHDM”). Thecondensation results in the loss of water molecules. The residues in theresulting polymer are derived from either terephthalic acid andcyclohexyl-1,4-dimethanol.

The polymer can also be functionalized by other reactants (e.g.,epoxides, isocyanates, and the like) during and after the polymerizationreaction. The incorporated reactants are also considered residues.

The terms “containing” or “including” are intended to be synonymous withthe term “comprising”, meaning that at least the named compound,element, particle, or method step, etc., is present in the compositionor article or method, but does not exclude the presence of othercompounds, catalysts, materials, particles, method steps, etc, even ifthe other such compounds, material, particles, method steps, etc., havethe same function as what is named, unless expressly excluded in theclaims.

As used herein, the term “alkyl” shall denote a hydrocarbon substituent.Alkyl groups suitable for use herein can be straight, branched, orcyclic, and can be saturated or unsaturated. The carbon units in thealkyl group is often included; for example (C₁₋₆)alkyl. Alkyl groupssuitable for use herein include any (C₁₋₂₀), (C₁₋₁₂), (C₁₋₅), or (C₁₋₃)alkyl groups. In various embodiments, the alkyl can be a C₁₋₅ straightchain alkyl group. In still other embodiments, the alkyl can be a C₁₋₃straight chain alkyl group. Specific examples of suitable alkyl groupsinclude, but are not limited to, methyl, ethyl, n-propyl, isopropyl,n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, octyl, decyl,dodecyl, cyclopentyl, and cyclohexyl groups. As used herein, the term“alkylene” shall mean a bivalent alkyl radical.

“Cycloalkyl” means a cyclic alkyl group having at least three carbonunits. The carbon units in the cycloalkyl group is often included; forexample (C₃₋₈)cycloalkyl. Nonlimiting examples of cycloalkyl includecyclopropyl, cyclobutyl, cyclohexyl, cycloheptyl, and the like.

“Bicycloalkyl” means a ring system with two fused cycloalkyl rings. Thebicycloalkyl ring system may be bridged or unbridged. The number ofcarbon units may be specified (e.g., C₆₋₁₀).

“Heterocyclyl” means a nonaromatic ring system containing one or moreheteroatoms including N, O, and S. The number and kind of heteroatomspresent may be specified. The size of the ring may also be specified. Anexample includes a 6- to 8-membered heterocyclyl containing 2 Nheteroatoms. Examples of a heterocyclyl groups include piperadinyl,piperazinyl, and pyrrolidine.

“Amorphous” means that the material will not exhibit a melting point bydynamic scanning calorimetry (“DSC”) after a scanning sequenceconsisting of cooling from the melt state (i.e. generally in the area of280-300° C.) and heating under typical ramp (both cooling and heating)rates of 20° C./minute under a nitrogen atmosphere with the temperaturerange covered by the scans is from −50° C. to 300° C.

“Semi-crystalline” means that the material exhibits a melting point asdetectable by DSC after a scanning sequence consisting of cooling fromthe melt state (i.e. generally in the area of 280-300° C.) and heatingunder typical ramp (both cooling and heating) rates of 20° C./minuteunder a nitrogen atmosphere with the temperature range covered by thescans is from −50° C. to 300° C. “Micro-crystalline” means that thematerial exhibits a melting point at as detected by DSC but typicallyremains visually clear due to small crystalline domain sizes or thatcoupled with small differences in the refractive indices betweenamorphous and crystalline domains.

Alkane dioic acids; such as heptanedioic acid, octanedioic acid,nonanedioic acid, decanedioic acid, undecanedioic acid, dodecanedioicacid, tridecanedioic acid, hexadecanedioic acid, octadecanedioic acid,or eicosanedioic acid; can be have terminal carboxylic acids or internalcarboxylic acids. For example, heptane dioic acid can be 1,7 heptanedioic acid, 1,6-heptane dioic acid, 1,5-heptane dioic acid, 1,4-heptanedioic acid, 2,6-heptane dioic acid, 3,5-heptane dioic acid, and thelike. The alkane group can be unbranched or branched. For example,heptane dioic acid can be 2-methylhexanedioic acid, 3-methylhexanedioicacid, 2-ethylpendanedioic acid, and the like.

“Epoxy silane” means a chemical that has at least one silane moiety andan epoxy moiety connected by a linker. Nonlimiting examples of epoxysilanes are as follows:

-   -   R is (C₁₋₁₂)alkyl;    -   A group is a (C₃₋₈)cycloalkyl ring system;    -   Linker is a bond, an (C₁₋₂₀)_(alkyl,) (C₃₋₈)cycloalkyl,        hetero(C₂₋₂₀)alkyl, or aryl.

The epoxy group of the epoxy silane can react with the polyesteramidesto incorporate the epoxy silane in the polymer. The epoxy silane can beincorporated in the reaction to synthesize the polymer, the epoxy silanecan be incorporated as an additive after the polymer is synthesized, orthe epoxy silane can be incorporated on the surface of articles formedfrom the polymer. By incorporating the epoxy silane into the polymer,the properties of the polymer can be modified. For example, the epoxysilane can be used to improve the adhesion of the polymer to varioussurfaces (e.g., glass surfaces). Specific examples of epoxy silanesinclude trimethoxy[2-7-oxabicyclo[4.1.0]hept-3-yl]ethyl]silane,triethoxy[2-7-oxabicyclo[4.1.0]hept-3-yl]ethyl]silane,(3-glycidyloxypropyl)trimethoxysilane,(3-glycidyloxypropyl)trimethoxysilane,diethoxy(3-glycidyloxypropyl)methylsilane,3-glycidoxypropyldimethylethoxysilane, 5,6-epoxyhexyltriethoxysilane,and the like.

“Isocyanate silane” means a chemical that has at least one silane moietyand an isocyanate moiety connected by a linker. Nonlimiting examples ofisocyanate silanes are as follows:

-   -   R is (C₁₋₁₂)alkyl;    -   Linker is a bond, an (C₁₋₂₀)alkyl,    -   (C₃₋₈)cycloalkyl, hetero(C₂₋₂₀)alkyl, or aryl.

The isocyanate group of the isocyanate silane can react with thepolyesteramides to incorporate the isocyanate silane in the polymer. Theisocyanate silane can be incorporated in the reaction to synthesize thepolymer, the isocyanate silane can be incorporated as an additive afterthe polymer is synthesized, or the isocyanate silane can be incorporatedon the surface of articles formed from the polymer. By incorporating theisocyanate silane into the polymer, the properties of the polymer can bemodified. For example, the isocyanate silane can be used to improve theadhesion of the polymer to various surfaces (e.g., glass surfaces).Nonlimiting examples of isocyanate silanes include3-isocyanotopropyltrimethoxysilane, 3-isocyanotopropyltriethoxysilaneand the like.

Compositions of Matter

The present application discloses a polyesteramide comprising: (a) adiamine component comprising: 1 to 99 mole % of diamine residues derivedfrom diamine which is a CH₂((C₃₋₈)cycloalkyl-NH₂)₂; (b) a diol componentcomprising: 1 to 99 mole % of diol residues derived from a diol which isa (C₃₋₈)cycloalkyl di((C₁₋₃)alkanol); (c) a diacid component comprising:10 to 100 mole % of diacid residues derived from a diacid which ischosen from HO₂C—(C₂₋₄₀)alkylene-CO₂H, or HO₂C—(C₃₋₁₀)cycloalkyl-CO₂H;wherein each cycloalkyl is unsubstituted or substituted by 1-4(C₁₋₃)alkyl, wherein the total mole % of the diacid component is 100mole %, and wherein the total mole % of the combined diol and diaminecomponent is 100 mole %.

In one embodiment, the polyesteramide comprises: (a) a diamine componentcomprising: 1 to 99 mole % of diamine residues derived from diaminewhich is a CH₂((C₃₋₈)cycloalkyl-NH₂)₂; (b) a diol component comprising:1 to 99 mole % of diol residues derived from a diol which is a(C₃₋₈)cycloalkyl di((C₁₋₃)alkanol); (c) a diacid component comprising:10 to 100 mole % of diacid residues derived from a diacid which ischosen from HO₂C—(C₂₋₂₀)alkylene-CO₂H, or HO₂C—(C₃₋₁₀)cycloalkyl-CO₂H;wherein each cycloalkyl is unsubstituted or substituted by 1-4(C₁₋₃)alkyl, wherein the total mole % of the diacid component is 100mole %, and wherein the total mole % of the combined diol and diaminecomponent is 100 mole %.

In one embodiment, the diol is chosen from cyclohexane-1,4-dimethanol,cyclohexane-1,3-dimethanol, cyclopentane-1,3-dimethanol,cyclobutane-1,3-dimethanol, cycloheptane-1,4-dimethanol, orcyclohexane-1,4-diethanol. In one class of this embodiment, the diolresidues are present at from about 15 mole % to about 75 mole %.

In one class of this embodiment, the diol is chosen fromcyclohexane-1,4-dimethanol or cyclohexane-1,3-dimethanol. In subclass ofthis class, the diol residues are present at from about 15 mole % toabout 75 mole %.

In one class of this embodiment, the diol is cyclohexane-1,4-dimethanol.In one class of this embodiment, the diol is cyclohexane-1,3-dimethanol.In one subclass of this class, the diol residues are present at fromabout 15 mole % to about 75 mole %.

In one class of this embodiment, the diol is cyclobutane-1,3-dimethanol.In one subclass of this class, the diol residues are present at fromabout 15 mole % to about 75 mole %.

In one class of this embodiment, the diol iscycloheptane-1,4-dimethanol. In one subclass of this class, the diolresidues are present at from about 15 mole % to about 75 mole %.

In one class of this embodiment, the diol is cyclohexane-1,4-diethanol.In one subclass of this class, the diol residues are present at fromabout 15 mole % to about 75 mole %.

In one embodiment, the diol residues are present at from about 5 mole %to about 90 mole %. In one embodiment, the diol residues are present atfrom about 10 mole % to about 80 mole %. In one embodiment, the diolresidues are present at from about 10 mole % to about 90 mole %. In oneembodiment, the diol residues are present at from about 15 mole % toabout 30 mole %. In one embodiment, the diol residues are present atfrom about 30 mole % to about 50 mole %. In one embodiment, the diolresidues are present at from about 50 mole % to about 70 mole %.

In one embodiment, the diol component further comprises an alkyleneglycol residue derived from H—[—O—CH₂—CH₂—(CH₂)_(n)—]_(m)—OH, wherein nis an integer from 0 to 2; and m is an integer from 2 to 50. In oneclass of this embodiment, the alkylene glycol residues are present from0.01 to 10 mole %. In one class of this embodiment, the alkylene glycolresidues are present from 0.01 to 5 mole %. In one class of thisembodiment, the alkylene glycol residues are present from 0.01 to 1 mole%. In one class of this embodiment, the alkylene glycol residues arepresent from 0.01 to 0.5 mole %. In one class of this embodiment, thealkylene glycol residues are present from 0.01 to 0.1 mole %.

In one embodiment, the diamine is chosen from4,4′-methylenebis(2-methylcyclohexylamine),4,4′-methylenebis(cyclohexylamine),4,4′-methylenebis(3-methylcyclohexan-1-amine),4,4′-methylenebis(2-methylcyclohexan-1-amine),4-((4-aminocyclohexyl)methyl)-2-methylcyclohexan-1-amine, or4,4′-methylenebis(2,6-dimethylcyclohexan-1-amine). In one class of thisembodiment, the diamine residues are present at from about 10 mole % toabout 85 mole %.

In one class of this embodiment, the diamine is chosen from4,4′-methylenebis(2-methylcyclohexylamine) or4,4′-methylenebis(cyclohexylamine). In one subclass of this class, thediamine residues are present at from about 10 mole % to about 85 mole %.

In one class of this embodiment, the diamine is4,4′-methylenebis(2-methylcyclohexylamine). In one subclass of thisclass, the diamine residues are present at from about 10 mole % to about85 mole %.

In one class of this embodiment, the diamine is4,4′-methylenebis(cyclohexylamine). In one subclass of this class, thediamine residues are present at from about 10 mole % to about 85 mole %.

In one class of this embodiment, the diamine is4,4′-methylenebis(3-methylcyclohexan-1-amine). In one subclass of thisclass, the diamine residues are present at from about 10 mole % to about85 mole %.

In one class of this embodiment, the diamine is4,4′-methylenebis(2-methylcyclohexan-1-amine). In one subclass of thisclass, the diamine residues are present at from about 10 mole % to about85 mole %.

In one class of this embodiment, the diamine is4-((4-aminocyclohexyl)methyl)-2-methylcyclohexan-1-amine. In onesubclass of this class, the diamine residues are present at from about10 mole % to about 85 mole %.

In one class of this embodiment, the diamine is4,4′-methylenebis(2,6-dimethylcyclohexan-1-amine). In one subclass ofthis class, the diamine residues are present at from about 10 mole % toabout 85 mole %.

In one embodiment, the diamine residues are present at from about 5 mole% to about 90 mole %. In one embodiment, the diamine residues arepresent at from about 10 mole % to about 80 mole %. In one embodiment,the diamine residues are present at from about 10 mole % to about 85mole %. In one embodiment, the diamine residues are present at fromabout 15 mole % to about 30 mole %. In one embodiment, the diamineresidues are present at from about 30 mole % to about 50 mole %. In oneembodiment, the diamine residues are present at from about 50 mole % toabout 70 mole %.

In one embodiment, the HO₂C—(C₂₋₄₀)alkylene-CO₂H is present from about40 mole % to about 70 mole % and the HO₂C—(C₃₋₁₀)cycloalkyl-CO₂H ispresent from about 30 mole % to about 60 mole %. In one embodiment, theHO₂C—(C₂₋₄₀)alkylene-CO₂H is present from about 50 mole % to about 60mole % and the HO₂C—(C₃₋₁₀)cycloalkyl-CO₂H is present from about 40 mole% to about 50 mole %.

In one embodiment, the HO₂C—(C₂₋₂₀)alkylene-CO₂H is present from about40 mole % to about 70 mole % and the HO₂C—(C₃₋₁₀)cycloalkyl-CO₂H ispresent from about 30 mole % to about 60 mole %. In one embodiment, theHO₂C—(C₂₋₂₀)alkylene-CO₂H is present from about 50 mole % to about 60mole % and the HO₂C—(C₃₋₁₀)cycloalkyl-CO₂H is present from about 40 mole% to about 50 mole %.

In one embodiment, the diacid is HO₂C—(C₂₋₂₀)alkylene-CO₂H. In one classof this embodiment, the diamine is chosen from4,4′-methylenebis(2-methylcyclohexylamine) or4,4′-methylenebis(cyclohexylamine). In one subclass of this class, thediol is cyclohexane-1,4-dimethanol.

In one embodiment, the diacid is HO₂C—(C₂₋₄₀)alkylene-CO₂H. In one classof this embodiment, the diamine is chosen from4,4′-methylenebis(2-methylcyclohexylamine) or4,4′-methylenebis(cyclohexylamine). In one subclass of this class, thediol is cyclohexane-1,4-dimethanol.

In one embodiment, the diacid is HO₂C—(C₃₋₁₀)cycloalkyl-CO₂H. In oneclass of this embodiment, the diamine is chosen from4,4′-methylenebis(2-methylcyclohexylamine) or4,4′-methylenebis(cyclohexylamine). In one subclass of this class, thediol is cyclohexane-1,4-dimethanol.

In one embodiment, the diacid is chosen from succinic acid, glutaricacid, adipic acid, heptanedioic acid, octanedioic acid, nonanedioic acid(e.g, azelaic acid), decanedioic acid (e.g, sebacic acid), undecanedioicacid, dodecanedioic acid, tridecanedioic acid, hexadecanedioic acid,octadecanedioic acid, eicosanedioic acid,9-[(Z)-non-3-enyl]-10-octylnonadecanedioic acid (dimer acid),9-nonyl-10-octylnonadecanedioic acid (hydrogenated dimer acid, Pripol1009), cyclobutane-1,3-dicarboxylic acid, cyclopentane-1,3-dicarboxylicacid, cyclohexane-1,4-dicarboxylic acid, cyclohexane-1,3-dicarboxylicacid, cycloheptane-1,4-dicarboxylic acid, cyclooctane-1,5-dicarboxylicacid, or cyclooctane-1,4-dicarboxylic acid. In one class of thisembodiment, the diamine is chosen from4,4′-methylenebis(2-methylcyclohexylamine) or4,4′-methylenebis(cyclohexylamine). In one subclass of this class, thediol is cyclohexane-1,4-dimethanol.

In one embodiment, the diacid is chosen from adipic acid,1,12-dodecanedioic acid, azelaic acid, sebacic acid,1,18-octadecanedioic acid, 9-nonyl-10-octylnonadecanedioic acid(hydrogenated dimer acid, Pripol 1009), cyclohexane-1,3-dicarboxylicacid or cyclohexane-1,4-dicarboxylic acid. In one class of thisembodiment, the diamine is chosen from4,4′-methylenebis(2-methylcyclohexylamine) or4,4′-methylenebis(cyclohexylamine). In one subclass of this class, thediol is cyclohexane-1,4-dimethanol. In one sub-subclass of thissubclass, the adipic acid or 1,12-dodecanedioic acid is present fromabout 40 mole % to about 70 mole % and the cyclohexane-1,3-dicarboxylicacid is present from about 30 mole % to about 60 mole %. In onesub-subclass of this subclass, the adipic acid or 1,12-dodecanedioicacid is present from about 50 mole % to about 60 mole % and thecyclohexane-1,3-dicarboxylic acid is present from about 40 mole % toabout 50 mole %.

In one embodiment, the diacid is chosen from succinic acid, glutaricacid, adipic acid, heptanedioic acid, octanedioic acid, nonanedioic acid(e.g., azelaic acid), decanedioic acid (e.g, sebacic acid),undecanedioic acid, dodecanedioic acid, tridecanedioic acid,hexadecanedioic acid, octadecanedioic acid, or eicosanedioic acid. Inone class of this embodiment, the diamine is chosen from4,4′-methylenebis(2-methylcyclohexylamine) or4,4′-methylenebis(cyclohexylamine). In one subclass of this class, thediol is cyclohexane-1,4-dimethanol.

In one embodiment, the diacid is chosen from adipic acid, or1,12-dodecanedioic acid. In one class of this embodiment, the diamine ischosen from 4,4′-methylenebis(2-methylcyclohexylamine) or4,4′-methylenebis(cyclohexylamine). In one subclass of this class, thediol is cyclohexane-1,4-dimethanol.

In one embodiment, the diacid is chosen fromcyclobutane-1,3-dicarboxylic acid, cyclopentane-1,3-dicarboxylic acid,cyclohexane-1,4-dicarboxylic acid, cyclohexane-1,3-dicarboxylic acid,cycloheptane-1,4-dicarboxylic acid, cyclooctane-1,5-dicarboxylic acid,or cyclooctane-1,4-dicarboxylic acid. In one class of this embodiment,the diamine is chosen from 4,4′-methylenebis(2-methylcyclohexylamine) or4,4′-methylenebis(cyclohexylamine). In one subclass of this class, thediol is cyclohexane-1,4-dimethanol.

In one embodiment, the diacid is cyclohexane-1,3-dicarboxylic acid. Inone class of this embodiment, the diamine is chosen from4,4′-methylenebis(2-methylcyclohexylamine) or4,4′-methylenebis(cyclohexylamine). In one subclass of this class, thediol is cyclohexane-1,4-dimethanol.

In one embodiment, the diacid is 9-nonyl-10-octylnonadecanedioic acid(hydrogenated dimer acid, Pripol 1009). In one class of this embodiment,the diamine is chosen from 4,4′-methylenebis(2-methylcyclohexylamine) or4,4′-methylenebis(cyclohexylamine). In one subclass of this class, thediol is cyclohexane-1,4-dimethanol.

In one embodiment, the polyesteramide further comprises branching agentresidues derived from a compound chosen from trimellitic acid,trimethylolpropane, trimethylolethane, glycerol, pentaerythritol, citricacid, tartaric acid, 3-hydroxyglutaric acid, glycerineerythritol,threitol, dipentaerythritol, sorbitol, trimellitic anhydride,pyromelltic dianhydride, trimesic acid, or dimethylol propionic acid.

In one class of this embodiment, the branching agent residues arepresent from about 0.01 to about 10 weight % based on the total weight %of the polyesteramide. In one class of this embodiment, the branchingagent residues are present from about 0.001 to about 10 weight % basedon the total weight % of the polyesteramide.

In one class of this embodiment, the branching agent residues arederived from trimellitic acid. In one class of this embodiment, thebranching agent residues are derived from trimethylolpropane. In oneclass of this embodiment, the branching agent residues are derived fromtrimethylolethane. In one class of this embodiment, the branching agentresidues are derived from glycerol. In one class of this embodiment, thebranching agent residues are derived from pentaerythritol. In one classof this embodiment, the branching agent residues are derived from citricacid. In one class of this embodiment, the branching agent residues arederived from tartaric acid. In one class of this embodiment, thebranching agent residues are derived from 3-hydroxyglutaric acid. In oneclass of this embodiment, the branching agent residues are derived fromglycerineerythritol. In one class of this embodiment, the branchingagent residues are derived from threitol. In one class of thisembodiment, the branching agent residues are derived fromdipentaerythritol. In one class of this embodiment, the branching agentresidues are derived from sorbitol. In one class of this embodiment, thebranching agent residues are derived from trimellitic anhydride. In oneclass of this embodiment, the branching agent residues are derived frompyromelltic dianhydride. In one class of this embodiment, the branchingagent residues are derived from trimesic acid. In one class of thisembodiment, the branching agent residues are derived from dimethylolpropionic acid.

The branching monomer may be added to the polyesteramide reactionmixture or blended with the polyesteramide in the form of a concentrateas described, for example, in U.S. Pat. Nos. 5,654,347 and 5,696,176,whose disclosure regarding branching monomers for polyesters isincorporated herein by reference.

In one embodiment, the polyesteramide has a glass transition temperatureof from about −30° C. to about 200° C. In one class of this embodiment,the polyesteramide has a glass transition temperature of from about −30°C. to about 20° C. In one class of this embodiment, the polyesteramidehas a glass transition temperature of from about −20° C. to about 20° C.In one class of this embodiment, the polyesteramide has a glasstransition temperature of from about −20° C. to about 0° C. In one classof this embodiment, the polyesteramide has a glass transitiontemperature of from about 0° C. to about 200° C. In one class of thisembodiment, the polyesteramide has a glass transition temperature offrom about 0° C. to about 20° C. In one class of this embodiment, thepolyesteramide has a glass transition temperature of from about 20° C.to about 90° C. In one class of this embodiment, the polyesteramide hasa glass transition temperature of from about 90° C. to about 130° C. Inone class of this embodiment, the polyesteramide has a glass transitiontemperature of from about 130° C. to about 200° C. In one class of thisembodiment, the polyesteramide has a glass transition temperature offrom about 90° C. to about 190° C.

In one embodiment, the polyesteramide has an inherent viscosity of fromabout 0.3 dL/g to about 2.0 dL/g as determined according to ASTMD2857-70. In one class of this embodiment, the polyesteramide has aninherent viscosity of from about 0.3 dL/g to about 1.4 dL/g asdetermined according to ASTM D2857-70. In one class of this embodiment,the polyesteramide has an inherent viscosity of from about 0.4 dL/g toabout 0.8 dL/g as determined according to ASTM D2857-70. In one class ofthis embodiment, the polyesteramide has an inherent viscosity of fromabout 0.4 dL/g to about 0.5 dL/g as determined according to ASTMD2857-70. In one class of this embodiment, the polyesteramide has aninherent viscosity of from about 0.5 dL/g to about 0.6 dL/g asdetermined according to ASTM D2857-70. In one class of this embodiment,the polyesteramide has an inherent viscosity of from about 0.6 dL/g toabout 0.7 dL/g as determined according to ASTM D2857-70. In one class ofthis embodiment, the polyesteramide has an inherent viscosity of fromabout 0.7 dL/g to about 0.8 dL/g as determined according to ASTMD2857-70. In one class of this embodiment, the polyesteramide has aninherent viscosity of from about 0.8 dL/g to about 1.4 dL/g asdetermined according to ASTM D2857-70. In one class of this embodiment,the polyesteramide has an inherent viscosity of from about 0.9 dL/g toabout 1.4 dL/g as determined according to ASTM D2857-70. In one class ofthis embodiment, the polyesteramide has an inherent viscosity of fromabout 1.0 dL/g to about 1.4 dL/g as determined according to ASTMD2857-70.

In one embodiment, the polyesteramide is amorphous or semicrystalline.In one class of this embodiment, the polyesteramide is amorphous. In oneclass of this embodiment, the polyesteramide is semicrystalline.

In one embodiment, the melt viscosity of the polyester(s) useful in theinvention is less than 30,000 poise as measured a 1 radian/second on arotary melt rheometer at 280° C. In another embodiment, the meltviscosity of the polyester(s) useful in the invention is less than20,000 poise as measured a 1 radian/second on a rotary melt rheometer at280° C. In one embodiment, the polyesteramide has a melt viscosity ofless than 10,000 poise as measured at 1 radian/second on a rotary meltrheometer at 280° C. In one embodiment, the polyesteramide has a meltviscosity of less than 9,000 poise as measured at 1 radian/second on arotary melt rheometer at 280° C. In one embodiment, the polyesteramidehas a melt viscosity of less than 8,000 poise as measured at 1radian/second on a rotary melt rheometer at 280° C. In one embodiment,the polyesteramide has a melt viscosity of less than 6,000 poise asmeasured at 1 radian/second on a rotary melt rheometer at 280° C. In oneembodiment, the polyesteramide has a melt viscosity of less than 6,000poise as measured at 1 radian/second on a rotary melt rheometer at 280°C. Viscosity at rad/sec is related to processability. Typical polymershave viscosities of less than 10,000 poise as measured at 1radian/second when measured at their processing temperature.

The present application also discloses a polyesteramide comprising: (a)a diamine component comprising: 1 to 99 mole % of diamine residuesderived from a diamine chosen from (C₂₋₂₀)alkyl diamine,CH₂((C₃₋₈)cycloalkyl-NH₂)₂,H₂N—((C₁₋₃)alkyl)₀₋₁-(C₃₋₈)cycloalkyl-((C₁₋₃)alkyl)₀₋₁-NH₂, 6- to8-membered heterocycyl containing 2 nitrogen atoms, orH₂N—((C₁₋₃)alkyl)₀₋₁-(C₆₋₁₀)bicyloalkyl-((C₁₋₃)alkyl)₀₋₁-NH₂ wherein thebicycyloalkyl is unbridged or bridged; (b) a diol component comprising:1 to 99 mole % of diol residues derived from a diol which is(C₃₋₈)cycloalkyl diol; (c) a diacid component comprising: 10 to 100 mole% of diacid residues derived from a diacid chosen fromHO₂C—(C₂₋₄₀)alkylene-CO₂H, or HO₂C—(C₃₋₁₀)cycloalkyl-CO₂H; wherein eachcycloalkyl is unsubstituted or substituted by 1-4 (C₁₋₃)alkyl, whereinthe total mole % of the diacid component is 100 mole %, wherein thetotal mole % of the combined diol and diamine component is 100 mole %.

In one embodiment, the polyesteramide comprises: (a) a diamine componentcomprising: 1 to 99 mole % of diamine residues derived from a diaminechosen from (C₂₋₂₀)alkyl diamine, CH₂((C₃₋₈)cycloalkyl-NH₂)₂,H₂N—((C₁₋₃)alkyl)₀₋₁-(C₃₋₈)cycloalkyl-((C₁₋₃)alkyl)₀₋₁-NH₂, 6- to8-membered heterocycyl containing 2 nitrogen atoms, orH₂N—((C₁₋₃)alkyl)₀₋₁-(C₆₋₁₀)bicyloalkyl-((C₁₋₃)alkyl)₀₋₁-NH₂ wherein thebicycyloalkyl is unbridged or bridged; (b) a diol component comprising:1 to 99 mole % of diol residues derived from a diol which is(C₃₋₈)cycloalkyl diol; (c) a diacid component comprising: 10 to 100 mole% of diacid residues derived from a diacid chosen fromHO₂C—(C₂₋₂₀)alkylene-CO₂H, or HO₂C—(C₃₋₁₀)cycloalkyl-CO₂H; wherein eachcycloalkyl is unsubstituted or substituted by 1-4 (C₁₋₃)alkyl, whereinthe total mole % of the diacid component is 100 mole %, wherein thetotal mole % of the combined diol and diamine component is 100 mole %.

In one embodiment, the diol is chosen from cyclobutane-1,3-diol,2,4-dimethylcyclobutane-1,3-diol, 2,4-diethylcyclobutane-1,3-diol,2,2-dimethylcyclobutane-1,3-diol, or2,2,4,4-tetramethylcyclobutane-1,3-diol. In one class of thisembodiment, the diol residues are present at from about 15 mole % toabout 65 mole %.

In one class of this embodiment, the diol is cyclobutane-1,3-diol. Inone subclass of this class, the diol residues are present at from about15 mole % to about 65 mole %.

In one class of this embodiment, the diol is2,4-dimethylcyclobutane-1,3-diol. In one subclass of this class, thediol residues are present at from about 15 mole % to about 65 mole %.

In one class of this embodiment, the diol is2,4-diethylcyclobutane-1,3-diol. In one subclass of this class, the diolresidues are present at from about 15 mole % to about 65 mole %.

In one class of this embodiment, the diol is2-dimethylcyclobutane-1,3-diol. In one subclass of this class, the diolresidues are present at from about 15 mole % to about 65 mole %.

In one class of this embodiment, the diol is2,2,4,4-tetramethylcyclobutane-1,3-diol. In one subclass of this class,the diol residues are present at from about 15 mole % to about 65 mole%.

In one embodiment, the diol residues are present at from about 5 mole %to about 90 mole %. In one embodiment, the diol residues are present atfrom about 10 mole % to about 80 mole %. In one embodiment, the diolresidues are present at from about 10 mole % to about 90 mole %. In oneembodiment, the diol residues are present at from about 15 mole % toabout 30 mole %. In one embodiment, the diol residues are present atfrom about 30 mole % to about 50 mole %. In one embodiment, the diolresidues are present at from about 50 mole % to about 70 mole %. In oneembodiment, the diol residues are present at from about 15 mole % toabout 65 mole %.

In one embodiment, the diol component further comprises an alkyleneglycol residue derived from H—[—O—CH₂—CH₂—(CH₂)_(n)-]_(m)—OH, wherein nis an integer from 0 to 2; and m is an integer from 2 to 50. In oneclass of this embodiment, the alkylene glycol residues are present from0.01 to 10 mole %. In one class of this embodiment, the alkylene glycolresidues are present from 0.01 to 5 mole %. In one class of thisembodiment, the alkylene glycol residues are present from 0.01 to 1 mole%. In one class of this embodiment, the alkylene glycol residues arepresent from 0.01 to 0.5 mole %. In one class of this embodiment, thealkylene glycol residues are present from 0.01 to 0.1 mole %.

In one embodiment, the diamine is (C₂₋₂₀)alkyl diamine. In one class ofthis embodiment, the diol residues are present at from about 35 mole %to about 85 mole %.

In one embodiment, the diamine is CH₂((C₃₋₈)cycloalkyl-NH₂)₂. In oneclass of this embodiment, the diol residues are present at from about 35mole % to about 85 mole %.

In one embodiment, the diamine isH₂N—((C₁₋₃)alkyl)₀₋₁-(C₃₋₈)cycloalkyl-((C₁₋₃)alkyl)₀₋₁-NH₂. In one classof this embodiment, the diol residues are present at from about 35 mole% to about 85 mole %.

In one embodiment, the diamine is 6- to 8-membered heterocycylcontaining 2 nitrogen atoms. In one class of this embodiment, the diolresidues are present at from about 35 mole % to about 85 mole %.

In one embodiment, the diamine isH₂N—((C₁₋₃)alkyl)₀₋₁-(C₆₋₁₀)bicyloalkyl-((C₁₋₃)alkyl)₀₋₁-NH₂ wherein thebicycyloalkyl is unbridged or bridged. In one class of this embodiment,the diol residues are present at from about 35 mole % to about 85 mole%.

In one embodiment, the diamine is chosen from4,4′-methylenebis(2-methylcyclohexylamine),4,4′-methylenebis(cyclohexylamine), 1,6-hexanediamine,2,4,5-trimethyl-1,6-hexanediamine,5-amino-1,3,3-trimethylcyclohexanemethylamine,1,4-bis(aminomethyl)cyclohexane, or2,2,4,4-tetramethyl-1,3-cyclobutanediamine. In one class of thisembodiment, the diol residues are present at from about 35 mole % toabout 85 mole %.

In one class of this embodiment, the diamine is chosen from4,4′-methylenebis(2-methylcyclohexylamine), or4,4′-methylenebis(cyclohexylamine). In one subclass of this class, thediol residues are present at from about 35 mole % to about 85 mole %.

In one class of this embodiment, the diamine is4,4′-methylenebis(2-methylcyclohexylamine). In one subclass of thisclass, the diol residues are present at from about 35 mole % to about 85mole %.

In one class of this embodiment, the diamine is4,4′-methylenebis(cyclohexylamine). In one subclass of this class, thediol residues are present at from about 35 mole % to about 85 mole %.

In one class of this embodiment, the diamine is 1,6-hexanediamine. Inone subclass of this class, the diol residues are present at from about35 mole % to about 85 mole %.

In one class of this embodiment, the diamine is2,4,5-trimethyl-1,6-hexanediamine. In one subclass of this class, thediol residues are present at from about 35 mole % to about 85 mole %.

In one class of this embodiment, the diamine is5-amino-1,3,3-trimethylcyclohexanemethylamine. In one subclass of thisclass, the diol residues are present at from about 35 mole % to about 85mole %.

In one class of this embodiment, the diamine is1,4-bis(aminomethyl)cyclohexane. In one subclass of this class, the diolresidues are present at from about 35 mole % to about 85 mole %.

In one class of this embodiment, the diamine is2,2,4,4-tetramethyl-1,3-cyclobutanediamine. In one subclass of thisclass, the diol residues are present at from about 35 mole % to about 85mole %.

In one embodiment, the diamine residues are present at from about 5 mole% to about 90 mole %. In one embodiment, the diamine residues arepresent at from about 10 mole % to about 80 mole %. In one embodiment,the diamine residues are present at from about 10 mole % to about 90mole %. In one embodiment, the diamine residues are present at fromabout 15 mole % to about 30 mole %. In one embodiment, the diamineresidues are present at from about 30 mole % to about 50 mole %. In oneembodiment, the diamine residues are present at from about 50 mole % toabout 70 mole %. In one embodiment, the diamine residues are present atfrom about 15 mole % to about 65 mole %. In one embodiment, the diamineresidues are present at from about 35 mole % to about 85 mole %.

In one embodiment, the HO₂C—(C₂₋₂₀)alkylene-CO₂H is present from about40 mole % to about 70 mole % and the HO₂C—(C₃₋₁₀)cycloalkyl-CO₂H ispresent from about 30 mole % to about 60 mole %. In one embodiment, theHO₂C—(C₂₋₄₀)alkylene-CO₂H is present from about 50 mole % to about 60mole % and the HO₂C—(C₃₋₁₀)cycloalkyl-CO₂H is present from about 40 mole% to about 50 mole %.

In one embodiment, the HO₂C—(C₂₋₂₀)alkylene-CO₂H is present from about40 mole % to about 70 mole % and the HO₂C—(C₃₋₁₀)cycloalkyl-CO₂H ispresent from about 30 mole % to about 60 mole %. In one embodiment, theHO₂C—(C₂₋₂₀)alkylene-CO₂H is present from about 50 mole % to about 60mole % and the HO₂C—(C₃₋₁₀)cycloalkyl-CO₂H is present from about 40 mole% to about 50 mole %.

In one embodiment, the diacid is HO₂C—(C₂₋₄₀)alkylene-CO₂H. In one classof this embodiment, the diamine is chosen from4,4′-methylenebis(2-methylcyclohexylamine) or4,4′-methylenebis(cyclohexylamine). In one subclass of this class, thediol is 2,2,4,4-tetramethylcyclobutane-1,3-diol.

In one embodiment, the diacid is HO₂C—(C₂₋₂₀)alkylene-CO₂H. In one classof this embodiment, the diamine is chosen from4,4′-methylenebis(2-methylcyclohexylamine) or4,4′-methylenebis(cyclohexylamine). In one subclass of this class, thediol is 2,2,4,4-tetramethylcyclobutane-1,3-diol.

In one embodiment, the diacid is HO₂C—(C₃₋₁₀)cycloalkyl-CO₂H. In oneclass of this embodiment, the diamine is chosen from4,4′-methylenebis(2-methylcyclohexylamine) or4,4′-methylenebis(cyclohexylamine). In one subclass of this class, thediol is 2,2,4,4-tetramethylcyclobutane-1,3-diol.

In one embodiment, the diacid is chosen from succinic acid, glutaricacid, adipic acid, heptanedioic acid, octanedioic acid, nonanedioic acid(e.g., azalaic acid), decanedioic acid (e.g., sebacic acid),undecanedioic acid, dodecanedioic acid, tridecanedioic acid,hexadecanedioic acid, octadecanedioic acid, eicosanedioic acid,9-[(Z)-non-3-enyl]-10-octylnonadecanedioic acid (dimer acid),9-nonyl-10-octylnonadecanedioic acid (hydrogenated dimer acid, Pripol1009), cyclobutane-1,3-dicarboxylic acid, cyclopentane-1,3-dicarboxylicacid, cyclohexane-1,4-dicarboxylic acid, cyclohexane-1,3-dicarboxylicacid, cycloheptane-1,4-dicarboxylic acid, cyclooctane-1,5-dicarboxylicacid, or cyclooctane-1,4-dicarboxylic acid. In one class of thisembodiment, the diamine is chosen from4,4′-methylenebis(2-methylcyclohexylamine) or4,4′-methylenebis(cyclohexylamine). In one subclass of this class, thediol is 2,2,4,4-tetramethylcyclobutane-1,3-diol.

In one embodiment, the diacid is chosen from adipic acid,1,12-dodecanedioic acid, azelaic acid, sebacic acid,1,18-octadecanedioic acid, 9-nonyl-10-octylnonadecanedioic acid(hydrogenated dimer acid, Pripol 1009), cyclohexane-1,3-dicarboxylicacid or cyclohexane-1,4-dicarboxylic acid. In one class of thisembodiment, the diamine is chosen from4,4′-methylenebis(2-methylcyclohexylamine) or4,4′-methylenebis(cyclohexylamine). In one subclass of this class, thediol is 2,2,4,4-tetramethylcyclobutane-1,3-diol. In one sub-subclass ofthis subclass, the adipic acid or 1,12-dodecanedioic acid is presentfrom about 40 mole % to about 70 mole % and thecyclohexane-1,3-dicarboxylic acid is present from about 30 mole % toabout 60 mole %. In one sub-subclass of this subclass, the adipic acidor 1,12-dodecanedioic acid is present from about 50 mole % to about 60mole % and the cyclohexane-1,3-dicarboxylic acid is present from about40 mole % to about 50 mole %.

In one embodiment, the diacid is chosen from succinic acid, glutaricacid, adipic acid, heptanedioic acid, octanedioic acid, nonanedioic acid(e.g., azelaic acid), decanedioic acid (e.g., sebacic acid),undecanedioic acid, dodecanedioic acid, tridecanedioic acid,hexadecanedioic acid, octadecanedioic acid, or eicosanedioic acid. Inone class of this embodiment, the diamine is chosen from4,4′-methylenebis(2-methylcyclohexylamine) or4,4′-methylenebis(cyclohexylamine). In one subclass of this class, thediol is 2,2,4,4-tetramethylcyclobutane-1,3-diol.

In one embodiment, the diacid is chosen from adipic acid, or1,12-dodecanedioic acid. In one class of this embodiment, the diamine ischosen from 4,4′-methylenebis(2-methylcyclohexylamine) or4,4′-methylenebis(cyclohexylamine). In one subclass of this class, thediol is 2,2,4,4-tetramethylcyclobutane-1,3-diol.

In one embodiment, the diacid is chosen fromcyclobutane-1,3-dicarboxylic acid, cyclopentane-1,3-dicarboxylic acid,cyclohexane-1,4-dicarboxylic acid, cyclohexane-1,3-dicarboxylic acid,cycloheptane-1,4-dicarboxylic acid, cyclooctane-1,5-dicarboxylic acid,or cyclooctane-1,4-dicarboxylic acid. In one class of this embodiment,the diamine is chosen from 4,4′-methylenebis(2-methylcyclohexylamine) or4,4′-methylenebis(cyclohexylamine). In one subclass of this class, thediol is 2,2,4,4-tetramethylcyclobutane-1,3-diol.

In one embodiment, the diacid is cyclohexane-1,3-dicarboxylic acid. Inone class of this embodiment, the diamine is chosen from4,4′-methylenebis(2-methylcyclohexylamine) or4,4′-methylenebis(cyclohexylamine). In one subclass of this class, thediol is 2,2,4,4-tetramethylcyclobutane-1,3-diol.

In one embodiment, the diacid is 9-nonyl-10-octylnonadecanedioic acid(hydrogenated dimer acid, Pripol 1009). In one class of this embodiment,the diamine is chosen from 4,4′-methylenebis(2-methylcyclohexylamine) or4,4′-methylenebis(cyclohexylamine). In one subclass of this class, thediol is 2,2,4,4-tetramethylcyclobutane-1,3-diol.

In one embodiment, the polyesteramide further comprises branching agentresidues derived from a compound chosen from trimellitic acid,trimethylolpropane, trimethylolethane, glycerol, pentaerythritol, citricacid, tartaric acid, 3-hydroxyglutaric acid, glycerineerythritol,threitol, dipentaerythritol, sorbitol, trimellitic anhydride,pyromelltic dianhydride, trimesic acid, or dimethylol propionic acid.

In one class of this embodiment, the branching agent residues arepresent from about 0.001 to about 10 weight % based on the total weightof the polyesteramide. In one class of this embodiment, the branchingagent residues are present from about 0.01 to about 10 weight % based onthe total weight of the polyesteramide. In one class of this embodiment,the branching agent residues are present at from about 0.001 to about 5weight % based on the total weight of the polyesteramide. In one classof this embodiment, the branching agent residues are present at fromabout 0.001 to about 1 weight % based on the total weight of thepolyesteramide. In one class of this embodiment, the branching agentresidues are present at from about 0.001 to about 0.05 weight % based onthe total weight of the polyesteramide. In one class of this embodiment,the branching agent residues are present at from about 0.001 to about0.01 weight % based on the total weight of the polyesteramide.

In one class of this embodiment, the branching agent residues arederived from trimellitic acid. In one class of this embodiment, thebranching agent residues are derived from trimethylolpropane. In oneclass of this embodiment, the branching agent residues are derived fromtrimethylolethane. In one class of this embodiment, the branching agentresidues are derived from glycerol. In one class of this embodiment, thebranching agent residues are derived from pentaerythritol. In one classof this embodiment, the branching agent residues are derived from citricacid. In one class of this embodiment, the branching agent residues arederived from tartaric acid. In one class of this embodiment, thebranching agent residues are derived from 3-hydroxyglutaric acid. In oneclass of this embodiment, the branching agent residues are derived fromglycerine erythritol. In one class of this embodiment, the branchingagent residues are derived from threitol. In one class of thisembodiment, the branching agent residues are derived fromdipentaerythritol. In one class of this embodiment, the branching agentresidues are derived from sorbitol. In one class of this embodiment, thebranching agent residues are derived from trimellitic anhydride. In oneclass of this embodiment, the branching agent residues are derived frompyromelltic dianhydride. In one class of this embodiment, the branchingagent residues are derived from trimesic acid. In one class of thisembodiment, the branching agent residues are derived from dimethylolpropionic acid.

The branching monomer may be added to the polyester reaction mixture orblended with the polyester in the form of a concentrate as described,for example, in U.S. Pat. Nos. 5,654,347 and 5,696,176, whose disclosureregarding branching monomers is incorporated herein by reference.

In one embodiment, the polyesteramide further comprises silane residuesderived from an epoxy silane or an isocyanate silane. In one class ofthis embodiment, the silane residues are present at from about 0.001 toabout 10 weight % based on the total weight of the polyesteramide. Inone class of this embodiment, the silane residues are present at fromabout 0.01 to about 10 weight % based on the total weight of thepolyesteramide. In one class of this embodiment, the silane residues arepresent at from about 0.001 to about 5 weight % based on the totalweight of the polyesteramide. In one class of this embodiment, thesilane residues are present at from about 0.001 to about 1 weight %based on the total weight of the polyesteramide. In one class of thisembodiment, the silane residues are present at from about 0.001 to about0.05 weight % based on the total weight of the polyesteramide. In oneclass of this embodiment, the silane residues are present at from about0.001 to about 0.01 weight % based on the total weight of thepolyesteramide.

In one embodiment, the polyesteramide has a glass transition temperatureof from about 0° C. to about 200° C. In one class of this embodiment,the polyesteramide has a glass transition temperature of from about 0°C. to about 20° C. In one class of this embodiment, the polyesteramidehas a glass transition temperature of from about 20° C. to about 90° C.In one class of this embodiment, the polyesteramide has a glasstransition temperature of from about 90° C. to about 130° C. In oneclass of this embodiment, the polyesteramide has a glass transitiontemperature of from about 130° C. to about 200° C. In one class of thisembodiment, the polyesteramide has a glass transition temperature offrom about 90° C. to about 190° C.

In one embodiment, the polyesteramide has an inherent viscosity of fromabout 0.3 dL/g to about 2.0 dL/g as determined according to ASTMD2857-70. In one class of this embodiment, the polyesteramide has aninherent viscosity of from about 0.3 dL/g to about 1.4 dL/g asdetermined according to ASTM D2857-70. In one class of this embodiment,the polyesteramide has an inherent viscosity of from about 0.4 dL/g toabout 0.8 dL/g as determined according to ASTM D2857-70. In one class ofthis embodiment, the polyesteramide has an inherent viscosity of fromabout 0.4 dL/g to about 0.5 dL/g as determined according to ASTMD2857-70. In one class of this embodiment, the polyesteramide has aninherent viscosity of from about 0.5 dL/g to about 0.6 dL/g asdetermined according to ASTM D2857-70. In one class of this embodiment,the polyesteramide has an inherent viscosity of from about 0.6 dL/g toabout 0.7 dL/g as determined according to ASTM D2857-70. In one class ofthis embodiment, the polyesteramide has an inherent viscosity of fromabout 0.7 dL/g to about 0.8 dL/g as determined according to ASTMD2857-70. In one class of this embodiment, the polyesteramide has aninherent viscosity of from about 0.8 dL/g to about 1.4 dL/g asdetermined according to ASTM D2857-70. In one class of this embodiment,the polyesteramide has an inherent viscosity of from about 0.9 dL/g toabout 1.4 dL/g as determined according to ASTM D2857-70. In one class ofthis embodiment, the polyesteramide has an inherent viscosity of fromabout 1.0 dL/g to about 1.4 dL/g as determined according to ASTMD2857-70.

In one embodiment, the polyesteramide is amorphous or semicrystalline.In one class of this embodiment, the polyesteramide is amorphous. In oneclass of this embodiment, the polyesteramide is semicrystalline.

In one embodiment, the melt viscosity of the polyester(s) useful in theinvention is less than 30,000 poise as measured a 1 radian/second on arotary melt rheometer at 280° C. In another embodiment, the meltviscosity of the polyester(s) useful in the invention is less than20,000 poise as measured a 1 radian/second on a rotary melt rheometer at280° C. In one embodiment, the polyesteramide has a melt viscosity ofless than 10,000 poise as measured at 1 radian/second on a rotary meltrheometer at 280° C. In one embodiment, the polyesteramide has a meltviscosity of less than 9,000 poise as measured at 1 radian/second on arotary melt rheometer at 280° C. In one embodiment, the polyesteramidehas a melt viscosity of less than 8,000 poise as measured at 1radian/second on a rotary melt rheometer at 280° C. In one embodiment,the polyesteramide has a melt viscosity of less than 6,000 poise asmeasured at 1 radian/second on a rotary melt rheometer at 280° C. In oneembodiment, the polyesteramide has a melt viscosity of less than 6,000poise as measured at 1 radian/second on a rotary melt rheometer at 280°C. Viscosity at rad/sec is related to processability. Typical polymershave viscosities of less than 10,000 poise as measured at 1radian/second when measured at their processing temperature.

Compositions

The present application also relates to compositions comprising thepolyesteramide disclosed herein.

The compositions can further comprise additive known to one skilled inthe art. In one embodiment, the compositions further comprises anadditive chosen from antioxidants, colorants, mold release agents, flameretardants, plasticizers, nucleating agents, UV stabilizers, UVabsorbers, thermal stabilizers, glass fibers, carbon fibers, fillers,impact modifiers, an epoxy silane, or isocyanate silane.

Examples of commercially available impact modifiers are well known inthe art and useful in this invention include, but are not limited to,ethylene-co-glycidyl methacrylate based impact modifiers,ethylene/propylene terpolymers based impact modifiers, styrene-basedblock copolymeric impact modifiers, and various acrylic core/shell typeimpact modifiers.

Thermal stabilizers are compounds known to be effective in stabilizingpolyesters during melt processing including but not limited tophosphoric acid, phosphorous acid, phosphonic acid, phosphinic acid,phosphonous acid, and various esters and salts thereof. The esters canbe alkyl, branched alkyl, substituted alkyl, difunctional alkyl, alkylethers, aryl, and substituted aryl. The number of ester groups presentin the particular phosphorus compound can vary from zero up to themaximum allowable based on the number of hydroxyl groups present on thephosphorus compound used.

Examples of thermal stabilizers include tributyl phosphate, triethylphosphate, tri-butoxyethyl phosphate, t-butylphenyl diphenyl phosphate,2-ethylhexyl diphenyl phosphate, ethyl dimethyl phosphate, isodecyldiphenyl phosphate, trilauryl phosphate, triphenyl phosphate, tricresylphosphate, trixylenyl phosphate, t-butylphenyl diphenylphosphate,resorcinol bis(diphenyl phosphate), tribenzyl phosphate, phenyl ethylphosphate, trimethyl thionophosphate, phenyl ethyl thionophosphate,dimethyl methylphosphonate, diethyl methylphosphonate, diethylpentylphosphonate, dilauryl methylphosphonate, diphenylmethylphosphonate, dibenzyl methylphosphonate, diphenylcresylphosphonate, dimethyl cresylphosphonate, dimethylmethylthionophosphonate, phenyl diphenylphosphinate, benzyldiphenylphosphinate, methyl diphenylphosphinate, trimethyl phosphineoxide, triphenyl phosphine oxide, tribenzyl phosphine oxide, 4-methyldiphenyl phosphine oxide, triethyl phosphite, tributyl phosphite,trilauryl phosphite, triphenyl phosphite, tribenzyl phosphite, phenyldiethyl phosphite, phenyl dimethyl phosphite, benzyl dimethyl phosphite,dimethyl methylphosphonite, diethyl pentylphosphonite, diphenylmethylphosphonite, dibenzyl methylphosphonite, dimethylcresylphosphonite, methyl dimethylphosphinite, methyldiethylphosphinite, phenyl diphenylphosphinite, methyldiphenylphosphinite, benzyl diphenylphosphinite, triphenyl phosphine,tribenzyl phosphine, Merpol A, and methyl diphenyl phosphine.

Reinforcing materials are also useful in the compositions of thisinvention. The reinforcing materials may include carbon filaments,silicates, mica, clay, talc, titanium dioxide, Wollastonite, glassflakes, glass beads and fibers, and polymeric fibers and combinationsthereof. The preferred reinforcing materials are glass, and it isfurther preferred to use fibrous glass filaments, mixtures of glass andtalc, glass and mica, and glass and polymeric fibers.

In one embodiment, the composition can further comprise a polymer chosenfrom a a polyesteramide other than those disclosed herein, a celluloseester, a polyvinyl chloride, a nylon, a polyester, a polyamide, apolystyrene, a polystyrene copolymer, a styrene acrylonitrile copolymer,an acrylonitrile butadiene styrene copolymer, apoly(methylmethacrylate), an acrylic copolymer, a poly(ethery-imide), apolyphenylene oxide, a polyphenylene sulfide, a polysulfone, apolysulfone ether, or a poly(ether-ketone) of an aromatic dihydroxycompound.

In one class of this embodiment, the polyesteramide is present fromabout 1 to about 99 wt % based on the total weight of the composition;and the polymer is present from about 1 to about 99 wt % based the totalweight of the composition. In one class of this embodiment, thepolyesteramide is present from about 5 to about 95 wt % based on thetotal weight of the composition; and the polymer is present from about 5to about 95 wt % based the total weight of the composition.

Articles

The present application relates to articles comprising thepolyesteramides or compositions disclosed herein. In one embodiment, thearticles are fibers, films, molded articles, containers, or sheeting.The methods of forming the polyesteramides or compositions disclosedherein into fibers, films, molded articles, containers, and sheeting arewell known in the art. Such articles may be produced from thepolyesteramides or compositions according to various embodiments of thepresent invention using any suitable method. Examples of such methods,depending on the type of shaped article, include, but are not limitedto, extrusion, calendaring, thermoforming, blow molding, extrusion blowmolding, injection molding, reactive injection molding, compressionmolding, casting, drafting, tentering, or blowing. Examples of potentialmolded articles include without limitation: medical devices such asdialysis equipment, medical packaging, healthcare supplies, commercialfood service products such as food pans, tumblers and storage boxes,baby bottles, food processors, blender and mixer bowls, utensils, waterbottles, crisper trays, washing machine fronts, and vacuum cleanerparts. Other potential molded articles could include, but are notlimited to, ophthalmic lenses and frames. For instance, this materialcan be used to make bottles, including but not limited to, baby bottles,as it is clear, tough, heat resistant, and displays good hydrolyticstability.

In one embodiment, the surface of the article is reacted, treated ormodified with an epoxy silane or an isocyanate silane. In one class ofthis embodiment, the surface of the article is reacted, treated ormodified with an epoxy silane. In one class of this embodiment, thesurface of the article is reacted, treated or modified with anisocyanate silane.

In one embodiment, the articles of manufacture are film(s) and/orsheet(s). The films and/or sheets useful in the present invention can beof any thickness which would be apparent to one of ordinary skill in theart. In one class of this embodiment, the film(s) of the invention havea thickness of no more than 40 mils. In one class of this embodiment,the film(s) of the invention have a thickness of no more than 35 mils.In one class of this embodiment, the film(s) of the invention have athickness of no more than 30 mils. In one class of this embodiment, thefilm(s) of the invention have a thickness of no more than 25 mils. Inone class of this embodiment, the film(s) of the invention have athickness of no more than 20 mils.

In one class of this embodiment, the sheet(s) of the invention have athickness of no less than 20 mils. In one class of this embodiment, thesheet(s) of the invention have a thickness of no less than 25 mils. Inone class of this embodiment, the sheet(s) of the invention have athickness of no less than 30 mils. In one class of this embodiment, thesheet(s) of the invention have a thickness of no less than 35 mils. Inone class of this embodiment, the sheet(s) of the invention have athickness of no less than 40 mils.

The methods of forming the polyesters into film(s) and/or sheet(s) arewell known in the art. Examples of film(s) and/or sheet(s) of theinvention including but not limited to extruded film(s) and/or sheet(s),calendered film(s) and/or sheet(s), compression molded film(s) and/orsheet(s), solution casted film(s) and/or sheet(s). Methods of makingfilm and/or sheet include but are not limited to extrusion, calendering,compression molding, and solution casting.

Examples of potential articles made from film and/or sheet useful in theinvention include, but are not limited, to uniaxially stretched film,biaxially stretched film, shrink film (whether or not uniaxially orbiaxially stretched, liquid crystal display film (including but notlimited to diffuser sheets, compensation films and protective films),thermoformed sheet, graphic arts film, outdoor signs, skylights,coating(s), coated articles, painted articles, laminates, laminatedarticles, and/or multiwall films or sheets.

In one embodiment, the article is a multilayer interlayer comprising apolyesteramide layer comprising a polyesteramide or polyesteramidecomposition disclosed herein.

In one class of this embodiment, the multilayer interlayer furthercomprises a first non-polyesteramide layer comprising apoly(vinylacetal) resin; and a first adhesive coating, wherein the firstadhesive coating is at least partially interposed between the firstnon-polyesteramide layer and the polyesteramide layer.

In one subclass of this class, a laminate comprises the multilayerinterlayer. In one subclass of this class, the first non-polyesteramidelayer further comprises a plasticizer.

In one sub-subclass of this subclass, a laminate comprises themultilayer interlayer.

“Graphic art film,” as used herein, is a film having a thermally-curableink (e.g., heat-curable ink or air-curable ink) or radiation-curable ink(e.g., ultra-violet-curable ink) printed thereon or therein. “Curable”refers to capable of undergoing polymerization and/or crosslinking. Inaddition to the ink, the graphic art film may optionally also includevarnishes, coatings, laminates, and adhesives.

In one embodiment, article is a graphic art film. In one class of thisembodiment, the graphic art film has at least one property chosen fromthermoformability, toughness, clarity, chemical resistance, Tg, andflexibility.

Graphic art films can be used in a variety of applications, such as, forexample, in-mold decorated articles, embossed articles, hard-coatedarticles. In one class of this embodiment, the graphic art film issmooth or textured.

Exemplary graphic art films include, but are not limited to, nameplates;membrane switch overlays (e.g., for an appliance); point of purchasedisplays; flat or in-mold decorative panels on washing machines; flattouch panels on refrigerators (e.g., capacitive touch pad arrays); flatpanel on ovens; decorative interior trim for automobiles (e.g., apolyester laminate) ; instrument clusters for automobiles; cell phonecovers; heating and ventilation control displays; automotive consolepanels; automotive gear shift panels; control displays or warningsignals for automotive instrument panels; facings, dials or displays onhousehold appliances; facings, dials or displays on washing machines;facings, dials or displays on dishwashers; keypads for electronicdevices; keypads for mobile phones, personal digital assistants (PDAs,or hand-held computers) or remote controls; displays for electronicdevices; displays for hand-held electronic devices such as phones andPDAs; panels and housings for mobile or standard phones; logos onelectronic devices; and logos for hand-held phones.

Multiwall film or sheet refers to sheet extruded as a profile consistingof multiple layers that are connected to each other by means of verticalribs. In one embodiment, the article is a multiwall film or sheet.Examples of multiwall film or sheet include but are not limited tooutdoor shelters (for example, greenhouses and commercial canopies).

Examples of extruded articles comprising the polyesteramides orcompositions disclosed herein that useful in this invention include, butare not limited to, thermoformed sheet, film for graphic artsapplications, outdoor signs, skylights, multiwall film, plastic film forplastic glass laminates, and liquid crystal display (LCD) films,including but not limited to, diffuser sheets, compensation films, andprotective films for LCDs.

Other articles within the scope of the invention include but are notlimited to safety/sport (examples including but not limited to: safetyshields, face shields, sports goggles [racquetball, ski, etc.], policeriot shields); corrugated sheet articles; recreation/outdoor vehiclesand devices (examples including but not limited to: lawn tractors, snowmobiles, motorcycle windshield, camper windows, golf cart windshield,jet ski); residential and commercial lighting (examples including butnot limited to: diffusers, office, home and commercial fixtures; HighIntensity Discharge (HID) Lighting); telecommunications/businessequipment/electronics (examples including but not limited to cell phonehousing, TV housing, computer housing, stereo housing, PDAs, etc.);optical media; tanning beds; multiwall sheet, extruded articles; rigidmedical packaging; intravenous components; dialysis filter housing;blood therapy containers; sterilization containers (for example, infantcare sterilization containers); pacifiers, tool handles (examplesincluding but not limited to screw drivers, hammer, etc.); thermoplasticarticles; sound barriers; automotive exterior (headlight covers,taillight covers, side windows, sunroof); rigid consumer/industrialpackaging; tubs; showers; hot tubs; machine guards; vending machinedisplay panels; meters; sports and recreation (examples: swimming poolenclosures, stadium seats, hockey rink, open air structures, skigondola); fish aquarium; ophthalmic products, decorative block windows;and interior automotive (instrument clusters).

In one embodiment, the article is a bottle. The methods of forming thepolyesteramides or compositions disclosed herein into bottles are wellknown in the art. Examples of bottles include but are not limited tobottles such as pharmaceutical bottles, baby bottles; water bottles;juice bottles; large commercial water bottles having a weight from 200to 800 grams; beverage bottles which include but are not limited to twoliter bottles, 20 ounce bottles, 16.9 ounce bottles; medical bottles;personal care bottles, carbonated soft drink bottles; hot fill bottles;water bottles; alcoholic beverage bottles such as beer bottles and winebottles; and bottles comprising at least one handle. These bottlesinclude but are not limited to injection blow molded bottles, injectionstretch blow molded bottles, extrusion blow molded bottles, andextrusion stretch blow molded bottles. Methods of making bottles includebut are not limited to extrusion blow molding, extrusion stretch blowmolding, injection blow molding, and injection stretch blow molding.Preforms (or parisons) can be used to make each of said bottles.

These bottles include, but are not limited to, injection blow moldedbottles, injection stretch blow molded bottles, extrusion blow moldedbottles, and extrusion stretch blow molded bottles. Methods of makingbottles include but are not limited to extrusion blow molding, extrusionstretch blow molding, thermoforming, injection blow molding, andinjection stretch blow molding.

In one embodiment, the article is a container. Examples includecontainers for cosmetics and personal care applications includingbottles, jars, vials and tubes; sterilization containers; buffet steampans; food pans or trays; frozen food trays; microwaveable food trays;hot fill containers, amorphous lids or sheets to seal or cover foodtrays; food storage containers; for example, boxes; tumblers, pitchers,cups, bowls, including but not limited to those used in restaurantsmallware; beverage containers; retort food containers; centrifugebowls; vacuum cleaner canisters, and collection and treatment canisters.

“Restaurant smallware,” as used herein, refers to any container used foreating or serving food. In one embodiment, the article is a restaurantsmallware. Examples of restaurant smallware include pitchers, cups, mugsoptionally including handles (including decorative mugs, single-ordouble walled mugs, pressurized mugs, vacuum mugs), bowls (e.g., servingbowls, soup bowls, salad bowls), and plates (e.g., eating and servingplates, such as buffet plates, saucers, dinner plates).

In one class of this embodiment, the restaurant smallware is capable ofwithstanding refrigerator temperatures ranging from greater than 0° C.(e.g., 2° C.) to 5° C. In one class of this embodiment, the restaurantsmallware can withstand steam treatments and/or commercial dishwasherconditions. In one class of this embodiment, the restaurant smallware iscapable of withstanding microwave conditions. In one class of thisembodiment, restaurant smallware has at least one property chosen fromtoughness, clarity, chemical resistance, Tg, hydrolytic stability, anddishwasher stability.

In one embodiment, the article is a medical device. Examples include butare not limited to medical devices comprising an ultraviolet light(UV)-curable, silicone-based coating, on at least a portion of a surfaceof a medical device.

In one embodiment, the article is a thermoplastic article, typically inthe form of sheet material, having a decorative material embeddedtherein.

“Food storage container,” as used herein, are capable of storing and/orserving hot and/or cold food and/or beverages at temperaturescustomarily used for storing and serving foods and beverages, e.g.,ranging from deep freezer temperatures to hot temperatures such as thosein a low temperature oven or those used in hot beverage dispensers. Inone embodiment, the article is a food storage container. In one class ofthis embodiment, the food storage container can be sealed to reduce therate of food oxidation. In one class of this embodiment, the foodstorage container can be used to display and serve the food to diningcustomers. In one class of this embodiment, the food storage containeris capable of being stored in a freezer, e.g., at temperatures less than0° C., such as temperatures ranging from −20 to 0° C. (e.g., −18° C.).In one class of this embodiment, the food storage container is capableof storing food in the refrigerator at temperatures ranging from greaterthan 0° C. (e.g., 2° C.) to 5° C. In one class of this embodiment, thefood storage container can withstand steam treatments and/or commercialdishwasher conditions. In one class of this embodiment, the food storagecontainer is capable of withstanding microwave conditions.

Examples of food storage containers include buffet steam pans, buffetsteam trays, food pans, hot and cold beverage dispensers (e.g.refrigerator beverage dispensers, automated hot or cold beveragedispensers), and food storage boxes.

In one class of this embodiment, food storage container has at least oneadditional property chosen from toughness, clarity, chemical resistance,Tg, and hydrolytic stability.

In one embodiment, the article is a thermoplastic article, which isobtained by applying heat and pressure to one or more laminates or“sandwiches”, wherein at least one of said laminates comprises, inorder, (1) at least one upper sheet material, (2) at least onedecorative material, and (3) at least one lower sheet material.Optionally, an adhesive layer may be used between (1) and (2) and/orbetween (2) and (3). Any of layers (1), (2) and/or (3) of the “sandwich”may comprise any of the polyesteramides or compositions disclosedherein.

“Ophthalmic product” as used herein, refers to prescription eyeglasslenses, nonprescription eyeglass lenses, sunglass lenses, and eyeglassand sunglass frames. In one embodiment, the article is an ophthalmicproduct. In one class of this embodiment, the ophthalmic product ischosen from tinted eyeglass lenses and hardcoated eyeglass lenses. Inone class of this embodiment, the eyeglass lenses, such as the tintedeyeglass lenses or hardcoated eyeglass lenses, comprise at least onepolarizing film or polarizing additive. In one class of this embodiment,when the ophthalmic product is a lens, the ophthalmic product has arefractive index ranging from 1.54 to 1.56. In one class of thisembodiment, the ophthalmic product can have at least one property chosenfrom toughness, clarity, chemical resistance (e.g., for withstandinglens cleaners, oils, hair products, etc.), Tg, and hydrolytic stability.

“Outdoor sign,” as used herein, refers to a surface formed from thepolyester described herein, or containing symbols (e.g., numbers,letters, words, pictures, etc.), patterns, or designs coated with thepolyester or polyester film described herein. In one embodiment, thearticle is an outdoor sign. In one class of this embodiment, the outdoorsign comprises printed symbols, patterns, or designs. In one class ofthis embodiment, the outdoor sign is capable of withstanding typicalweather conditions, such as rain, snow, ice, sleet, high humidity, heat,wind, sunlight, or combinations thereof, for a sufficient period oftime, e.g., ranging from one day to several years or more.

Exemplary outdoor signs include, but are not limited to, billboards,neon signs, electroluminescent signs, electric signs, fluorescent signs,and light emitting diode (LED) displays. Other exemplary outdoor signsinclude, but are not limited to, painted signs, vinyl decorated signs,thermoformed signs, and hardcoated signs.

In one class of this embodiment, the outdoor sign has at least oneproperty chosen from thermoformability, toughness, clarity, chemicalresistance, and Tg.

A “vending machine display panel,” as used herein, refers to a front orside panel on a vending machine that allows a customer to view the itemsfor sale, or advertisement regarding such items. In one embodiment, thearticle is a vending machine display panel. In one class of thisembodiment, the vending machine display panel is a visually clear panelof a vending machine through which a consumer can view the items onsale. In one class of this embodiment, the vending machine display panelcan have sufficient rigidity to contain the contents within the machineand/or to discourage vandalism and/or theft. In one class of thisembodiment, the vending machine display panel can have dimensions wellknown in the art, such as planar display panels in snack, beverage,popcorn, or sticker/ticket vending machines, and capsule display panelsas in, e.g., gumball machines or bulk candy machines. In one class ofthis embodiment, the vending machine display panel can optionallycontain advertising media or product identification indicia. Suchinformation can be applied by methods well known in the art, e.g., silkscreening.

In one class of this embodiment, the vending machine display panel canbe resistant to temperatures ranging from −100 to 120° C. In anotherembodiment, the vending machine display panel can be UV resistant by theaddition of, e.g., at least one UV additive, as disclosed herein. In oneclass of this embodiment, the vending machine display panel has at leastone property chosen from thermoformability, toughness, clarity, chemicalresistance, and Tg.

“Point of purchase display,” as used herein, refers to a wholly orpartially enclosed casing having at least one visually clear panel fordisplaying an item. Point of purchase displays are often used in retailstores to for the purpose of catching the eye of the customer. In oneembodiment, the article is a point of purchase display. Exemplary pointof purchase displays include enclosed wall mounts, countertops, enclosedposter stands, display cases (e.g., trophy display cases), sign frames,and cases for computer disks such as CDs and DVDs. The point of purchasedisplay can include shelves, and additional containers, such as holdersfor magazines or pamphlets. One of ordinary skill in the art can readilyenvision the shape and dimensions for the point of purchase displaydepending on the item to be displayed. For example, the display can beas small as a case for jewelry, or a larger enclosed cabinet fordisplaying multiple trophies. In one class of this embodiment, the pointof purchase display has at least one property chosen from toughness,clarity, chemical resistance, Tg, and hydrolytic stability.

“Intravenous component,” as used herein, refers to components made froma polymeric material used for administering fluids (e.g., medicaments,nutrients) to the bloodstream of a patient. In one embodiment, thearticle is an intravenous component. In one class of this embodiment,the intravenous component is a rigid component.

Exemplary intravenous components include y-site connector assemblies,luer components, filters, stopcocks, manifolds, and valves. A y-siteconnector has a “Y” shape including a first arm having a first passage,a second arm having a second passage, and a third arm connected withsaid first and second arms and having a third passage communicating withsaid first and second passages. Luer components can include luer locks,connections, and valves.

In one class of this embodiment, the intravenous component can withstandsterilization treatments, such as high pressure steam sterilization,ethylene oxide gas sterilization, radiation sterilization, anddry-heating sterilization. In one class of this embodiment, theintravenous component has at least one property chosen from toughness,clarity, chemical resistance, Tg, and hydrolytic stability.

A “dialysis filter housing,” as used herein, refers to a protectivecasing having a plurality of openings for holding a plurality of hollowfibers or tubing, which can be used for introducing and discharging adialyzate to a patient. In one embodiment, the article is a dialysisfilter housing. In one class of this embodiment, a cross-sectional areaof one opening in the protective casing of the dialysis filter housingranges from 0.001 cm² to less than 50 cm². In one class of thisembodiment, the dialysis filter housing has at least one property chosenfrom toughness, clarity, chemical resistance, Tg, and hydrolyticstability.

“Blood therapy containers,” as used herein, refers to those containersused in administering and withdrawing blood to and from a patient. Inone embodiment, the article is a blood therapy container. Exemplaryblood therapy containers include oxygenators, cassettes, centrifugebowls, collection and treatment canisters, pump cartridges, venal porthousings, and dialyzer housings. Oxygenators can remove carbon dioxidefrom the venous blood of the patient, introduce oxygen to the withdrawnblood to convert it into arterial blood, and introduce the oxygenatedblood to the patient. Other containers can be used to temporarily housethe withdrawn or stored blood prior to its administration to thepatient.

In one class of this embodiment, the blood therapy container canwithstand sterilization treatments, such as high pressure steamsterilization, ethylene oxide gas sterilization, radiationsterilization, and dry-heating sterilization. In one class of thisembodiment, the blood therapy container has at least one property chosenfrom toughness, clarity, chemical resistance, Tg, and hydrolyticstability.

“Appliance parts,” as used herein, refers to a rigid piece used inconjunction with an appliance. In one embodiment, the article is anappliance part. In one class of this embodiment, the appliance part ispartly or wholly separable from the appliance. In one class of thisembodiment, the appliance part is one that is typically made from apolymer. In one embodiment, the appliance part is visually clear.

Exemplary appliance parts include those requiring toughness anddurabilty, such as cups and bowls used with food processers, mixers,blenders, and choppers; parts that can withstand refrigerator andfreezer temperatures (e.g., refrigerator temperatures ranging fromgreater than 0° C. (e.g., 2° C.) to 5° C., or freezer temperatures,e.g., at temperatures less than 0° C., such as temperatures ranging from−20 to 0° C., e.g., −18° C.), such as refrigerator and freezer trays,bins, and shelves; parts having sufficient hydrolytic stability attemperatures up to 90° C., such as washing machine doors, steam cleanercanisters, tea kettles, and coffee pots; and vacuum cleaner canistersand dirt cups.

In one class of this embodiment, these appliance parts have at least oneproperty chosen from toughness, clarity, chemical resistance, Tg,hydrolytic stability, and dishwasher stability. The appliance part canalso be chosen from steam cleaner canisters, which, in one embodiment,can have at least one property chosen from toughness, clarity, chemicalresistance, Tg, and hydrolytic stability.

In one class of this embodiment, the polyesteramides useful in theappliance part has a T_(g) of 105° C. to 140° C. and the appliance partis chosen from vacuum cleaner canisters and dirt cups. In one class ofthis embodiment, the polyesteramides useful in the appliance part has aT_(g) of 120 to 200° C. and the appliance part is chosen from steamcleaner canisters, tea kettles and coffee pots.

“Skylight,” as used herein, refers to a light permeable panel secured toa roof surface such that the panel forms a portion of the ceiling. Inone embodiment, the article is a skylight. In one class of thisembodiment, the panel is rigid, e.g., has dimensions sufficient toachieve stability and durability, and such dimensions can readiliy bedetermined by one skilled in the art. In one class of this embodiment,the skylight panel has a thickness greater than 3/16 inches, such as athickness of at least ½ inches.

In one class of this embodiment, the skylight panel is visually clear.In one embodiment, the skylight panel can transmit at least 35% visiblelight, at least 50%, at least 75%, at least 80%, at least 90%, or evenat least 95% visible light. In one class of this embodiment, theskylight panel comprises at least one UV additive that allows theskylight panel to block up to 80%, 90%, or up to 95% UV light.

In one class of this embodiment, the skylight has at least one propertychosen from thermoformability, toughness, clarity, chemical resistance,and Tg.

“Outdoor shelters,” as used herein, refer to a roofed and/or walledstructure capable of affording at least some protection from theelements, e.g., sunlight, rain, snow, wind, cold, etc., having at leastone rigid panel. In one embodiment, the article is an outdoor shelter.In one class of this embodiment, the outdoor shelter has at least a roofand/or one or more walls. In one class of this embodiment, the outdoorshelter has dimensions sufficient to achieve stability and durability,and such dimensions can readiliy be determined by one skilled in theart. In one class of this embodiment, the outdoor shelter panel has athickness greater than 3/16 inches.

In one class of this embodiment, the outdoor shelter panel is visuallyclear. In one class of this embodiment, the outdoor shelter panel cantransmit at least 35% visible light, at least 50%, at least 75%, atleast 80%, at least 90%, or even at least 95% visible light. In oneclass of this embodiment, the outdoor shelter panel comprises at leastone UV additive that allows the outdoor shelter to block up to 80%, 90%,or up to 95% UV light.

Exemplary outdoor shelters include security glazings, transportationshelters (e.g., bus shelters), telephone kiosks, and smoking shelters.In one class of this embodiment, where the shelter is a transportationshelter, telephone kiosk, or smoking shelter, the shelter has at leastone property chosen from thermoformability, toughness, clarity, chemicalresistance, and Tg. In one class of this embodiment, where the shelteris a security glazing, the shelter has at least one property chosen fromtoughness, clarity, chemical resistance, and Tg.

A “canopy,” as used herein, refers to a roofed structure capable ofaffording at least some protection from the elements, e.g., sunlight,rain, snow, wind, cold, etc. In one embodiment, the roofed structurecomprises, either in whole or in part, at least one rigid panel, e.g.,has dimensions sufficient to achieve stability and durability, and suchdimensions can readily be determined by one skilled in the art. In oneembodiment, the article is a canopy. In one class of this embodiment,the canopy panel has a thickness greater than 3/16 inches, such as athickness of at least ½ inches.

In one class of this embodiment, the canopy panel is visually clear. Inone embodiment, the canopy panel can transmit at least 35% visiblelight, at least 50%, at least 75%, at least 80%, at least 90%, or evenat least 95% visible light. In one class of this embodiment, the canopypanel comprises at least one UV additive that allows the canopy to blockup to 80%, 90%, or up to 95% UV light.

Exemplary canopies include covered walkways, roof lights, sun rooms,airplane canopies, and awnings. In one embodiment, the canopy has atleast one property chosen from toughness, clarity, chemical resistance,Tg, and flexibility.

An “optical medium,” as used herein, refers to an information storagemedium in which information is recorded by irradiation with a laserbeam, e.g., light in the visible wavelength region, such as light havinga wavelength ranging from 600 to 700 nm. By the irradiation of the laserbeam, the irradiated area of the recording layer is locally heated tochange its physical or chemical characteristics, and pits are formed inthe irradiated area of the recording layer. Since the opticalcharacteristics of the formed pits are different from those of the areahaving been not irradiated, the digital information is opticallyrecorded. The recorded information can be read by reproducing proceduregenerally comprising the steps of irradiating the recording layer withthe laser beam having the same wavelength as that employed in therecording procedure, and detecting the light-reflection differencebetween the pits and their periphery. In one embodiment, the article isan optical medium.

In one class of this embodiment, the optical medium comprises atransparent disc having a spiral pregroove, a recording dye layer placedin the pregroove on which information is recorded by irradiation with alaser beam, and a light-reflecting layer. The optical medium isoptionally recordable by the consumer. In one class of this embodiment,the optical medium is chosen from compact discs (CDs) and digital videodiscs (DVDs). The optical medium can be sold with prerecordedinformation, or as a recordable disc.

In one class of this embodiment, at least one of the following comprisesthe polyesteramides or compositions disclosed herein: the substrate, atleast one protective layer of the optical medium, and the recordinglayer of the optical medium. In one class of this embodiment, theoptical medium has at least one property chosen from toughness, clarity,chemical resistance, Tg, and hydrolytic stability.

“Infant-care sterilization container,” as used herein, refers to acontainer configured to hold infant-care products for use in in-homesterilization of the infant-care products. In one embodiment, thearticle is an infant-care sterilization container. In one class of thisembodiment, the infant-care sterilization container is a baby bottlesterilization container. In one class of this embodiment, infant-caresterilization containers have at least one additional property chosenfrom toughness, clarity, chemical resistance, Tg, hydrolytic stability,and dishwasher stability.

“Pacifiers” as used herein, comprise a flexible nipple (e.g., for aninfant to suck and/or bite) surrounded by a rigid mouth shield, wherethe rigid mouth shield is optionally connected to a handle, allowing theinfant or supervising adult a convenient structure for gripping and/orholding the pacifier. The handle may be rigid or flexible. In oneembodiment, the article is a pacifier.

In one class of this embodiment, the pacifier can be made of multiplecomponents. For example, the nipple can pass through an aperture in thecenter of the mouth shield. The handle may or may not be integrallyconnected to the mouth shield. The handle can be rigid or flexible.

In one class of this embodiment, the nipple and mouth shield of thepacifier is formed as an integral unit. Generally, the selection ofplastic is governed by the need to provide a relatively rigid mountshield and handle. In one class of this embodiment, the nipple of thepacifier may be more rigid yet still be desirable for an infant to suckor bite.

In one class of this embodiment, pacifiers have at least one propertychosen from toughness, clarity, chemical resistance, Tg, hydrolyticstability, and dishwasher stability.

A “retort food container,” as used herein, refers to flexible containeror pouch for storing food and/or beverages, in which the food and/orbeverage is hermetically sealed for long-term unrefrigerated storage.The food can be sealed under vacuum or an inert gas. The retort foodcontainer can comprise at least one polyester layer, e.g., a singlelayer or multi-layer container. In one embodiment, the article is aretort food container. In one class of this embodiment, a multi-layercontainer includes a light reflecting inner layer, e.g., a metallizedfilm.

In one class of this embodiment, at least one foodstuff chosen fromvegetables, fruit, grain, soups, meat, meat products, dairy products,sauces, dressings, and baking supplies is contained in the retort foodcontainer.

In one class of this embodiment, the retort food container has at leastone property chosen from toughness, clarity, chemical resistance, Tg,and hydrolytic stability.

A “glass laminate,” as used herein, refers to at least one coating on aglass, where at least one of the coatings comprises the polyesteramide.The coating can be a film or a sheet. The glass can be clear, tinted, orreflective. In one embodiment, the article is a glass laminate. In oneclass of this embodiment, the laminate is permanently bonded to theglass, e.g., applying the laminate under heat and pressure to form asingle, solid laminated glass product. One or both faces of the glasscan be laminated. In one class of this embodiment, the glass laminatecontains more than one coating comprising the polyesteramide or thecompositions disclosed herein. In one class of this embodiment, theglass laminate comprises multiple glass substrates, and more than onecoating comprising the polyester compositions of the present invention.

Exemplary glass laminates include windows (e.g., windows for high risebuildings, building entrances), glass walls or sides, glass roofing,safety glass, windshields for transportation applications (e.g.,automotive, buses, jets, armored vehicles), bullet proof or resistantglass, security glass (e.g., for banks), hurricane proof or resistantglass, airplane canopies, mirrors, solar glass panels, flat paneldisplays, and blast resistant windows. The glass laminate can bevisually clear, be frosted, etched, or patterned.

In one class of this embodiment, the glass laminate can be UV resistantby the addition of, e.g., at least one UV additive, as disclosed herein.

Methods for laminating the films and/or sheets of the present inventionto the glass are well known to one of ordinary skill in the art.Lamination without the use of an adhesive layer may be performed byvacuum lamination. To obtain an effective bond between the glass layerand the laminate, in one embodiment, the glass has a low surfaceroughness.

Alternatively, a double-sided adhesive tape, an adhesive layer, or agelatin layer, obtained by applying, for example, a hotmelt, a pressure-or thermo-sensitive adhesive, or a UV or electron-beam curable adhesive,can be used to bond the laminate of the present invention to the glass.The adhesive layer may be applied to the glass sheet, to the laminate,or to both, and may be protected by a stripping layer, which can beremoved just before lamination.

In one class of this embodiment, the glass laminate has at least oneproperty chosen from toughness, clarity, chemical resistance, hydrolyticstability, surface energy, and Tg.

Processes

The present application also discloses a process for the preparation ofa polyesteramide which comprises: (1) reacting a reaction mixturecomprising: (i) 5 to 25 mole % of an at least one diol; and (ii) 50 to75 mole % of at least one diacid; in a reaction zone at a firsttemperature, at a first pressure, and for a first time sufficient toprovide at least one reaction product comprising 1 to 2 residues derivedfrom the at least one diacid and 1 residue of the at least one diol; (2)adding 5 to 25 mole % of a diamine and at least 25 mole % of water tothe reaction zone comprising the at least one reaction product; and (3)reacting the diamine with the at least one reaction product at a secondtemperature, at a second pressure, and for a second time sufficient toprovide the polyesteramide; wherein the mole % of the diol, diacid, ordiamine is based on the total moles of the diol, diacid and diamine, andwherein the mole % of the water is based on the total moles of thediacid and water.

In one embodiment, the water in step (2) is added at at least 1 mole %.In one embodiment, the water in step (2) is added at at least 5 mole %.In one embodiment, the water in step (2) is added at at least 10 mole %.In one embodiment, the water in step (2) is added at at least 15 mole %.In one embodiment, the water in step (2) is added at at least 20 mole %.

Step (1)

Reaction times for Step (1) are dependent upon the selectedtemperatures, pressures, and feed mole ratios of the at least one dioland the at least one diacid. In one embodiment, the first time is fromabout 5 min to about 24 hours. In one embodiment, the first time is fromabout 20 min to about 24 hours. In one embodiment, the first time isfrom about 5 min to about 6 hours. In one embodiment, the first time isfrom about 1 hour to about 24 hours. In one embodiment, the first timeis from about 1 hours to about 6 hours.

The temperature for Step (1), can be maintained at one temperature orvariable temperatures. In one embodiment, the first temperature is atleast one temperature in the range of from about 100° C. to about 300°C. In one embodiment, the first temperature is at least one temperaturein the range of from about 200° C. to about 300° C.

The pressure for Step (1) the pressure can be maintained at one pressureor variable pressures. In one embodiment, the first pressure is at leastone pressure in the range of from about 0 torr absolute to about 5171torr absolute. In one embodiment, the first pressure is at least onepressure in the range of from about 0 torr to about 2585 torr absolute.In one embodiment, the first pressure is at least one pressure in therange of from about 0 torr absolute to about 1551 torr absolute. In oneembodiment, the first pressure is at least one pressure in the range offrom about 0 torr absolute to about 776 torr absolute.

Catalysts can be used to catalyze the reaction of Step (1). In oneembodiment, Step (1) further comprises a catalyst. Examples of catalyststhat can be used are based on titanium, tin, gallium, zinc, antimony,cobalt, manganese, germanium, alkali metals, particularly lithium andsodium, alkaline earth compounds, aluminum compounds, combinations ofaluminum compounds with lithium hydroxide or sodium hydroxide. In oneclass of this embodiment, the catalyst is based on titanium or tin. Tincompounds are useful for polyesters containing TMCD as disclosed in U.S.Pat. No. 8,101,705 B2 and can be used in the process disclosed herein.

In one class of this embodiment, the catalyst is present from 1 to 500ppm. In one subclass of this class, the catalyst is a tin catalyst. Inone subclass of this class, the catalyst is a titanium catalyst.

In one class of this embodiment, the catalyst is present from 1 to 300ppm. In one subclass of this class, the catalyst is a tin catalyst. Inone subclass of this class, the catalyst is a titanium catalyst.

In one class of this embodiment, the catalyst is present from 5 to 125ppm. In one subclass of this class, the catalyst is chosen from a tincatalyst or a titanium catalyst. In one subclass of this class, thecatalyst is a tin catalyst. In one subclass of this class, the catalystis a titanium catalyst.

In one class of this embodiment, the catalyst is present from 10 to 100ppm. In one subclass of this class, the catalyst is chosen from a tincatalyst or a titanium catalyst. In one subclass of this class, thecatalyst is a tin catalyst. In one subclass of this class, the catalystis a titanium catalyst.

Examples of suitable titanium compounds include titanium(IV)2-ethylhexyloxide (e.g., Tyzor® TOT), titanium(IV)(triethanolaminato)isopropoxide (e.g., Tyzor® TE), tetraisopropyltitanate, titanium diisopropoxide bis(acetylacetonate), and tetrabutyltitanate (e.g., Tyzor® TBT). Examples of suitable tin compounds includebutyltin tris-2-ethylhexanoate, butylstannoic acid, stannous oxalate,dibutyltin oxide.

Step (3)

Reaction times for Step (3) are dependent upon the selectedtemperatures, pressures, and feed mole ratios of the at least one dioland the at least one diacid. In one embodiment, the first time is fromabout 5 min to about 24 hours. In one embodiment, the first time is fromabout 20 min to about 24 hours. In one embodiment, the first time isfrom about 5 min to about 6 hours. In one embodiment, the first time isfrom about 1 hour to about 24 hours. In one embodiment, the first timeis from about 1 hours to about 6 hours.

For Step (3), the temperature can be at one temperature or variabletemperatures. In one embodiment, the second temperature is at least onetemperature in the range of from about 0° C. to about 350° C. In oneembodiment, the second temperature is at least one temperature in therange of from about 32° C. to about 350° C. In one embodiment, thesecond temperature is at least one temperature in the range of fromabout 50° C. to about 350° C. In one embodiment, the second temperatureis at least one temperature in the range of from about 100° C. to about350° C. In one embodiment, the second temperature is at least onetemperature in the range of from about 200° C. to about 350° C. In oneembodiment, the second temperature is at least one temperature in therange of from about 250° C. to about 350° C.

The pressure for Step (3) the pressure can be maintained at one pressureor variable pressures. In one embodiment, the second pressure is atleast one pressure in the range of from about 0.1 torr absolute to about760 torr absolute. In one embodiment, the second pressure is at leastone pressure in the range of from about 0.1 torr absolute to about 100torr absolute. In one embodiment, the second pressure is at least onepressure in the range of from about 0.1 torr absolute to about 50 torrabsolute. In one embodiment, the second pressure is at least onepressure in the range of from about 0.1 torr absolute to about 10 torrabsolute. In one embodiment, the first pressure is at least one pressurein the range of from about 0.1 torr absolute to about 5 torr absolute.

Step (3) can be conducted by blowing hot nitrogen gas over the reactionmixture.

Catalysts can be used to catalyze the reaction of Step (3). In oneembodiment, Step (3) further comprises a catalyst. Examples of catalyststhat can be used are based on titanium, tin, gallium, zinc, antimony,cobalt, manganese, germanium, alkali metals, particularly lithium andsodium, alkaline earth compounds, aluminum compounds, combinations ofaluminum compounds with lithium hydroxide or sodium hydroxide. In oneclass of this embodiment, the catalyst is based on titanium or tin. Tincompounds are useful for polyesters containing TMCD as disclosed in U.S.Pat. No. 8,101,705 B2 and can be used in the process disclosed herein.

In one class of this embodiment, the catalyst is present from 1 to 500ppm. In one subclass of this class, the catalyst is a tin catalyst. Inone subclass of this class, the catalyst is a titanium catalyst.

In one class of this embodiment, the catalyst is present from 1 to 300ppm. In one subclass of this class, the catalyst is a tin catalyst. Inone subclass of this class, the catalyst is a titanium catalyst.

In one class of this embodiment, the catalyst is present from 5 to 125ppm. In one subclass of this class, the catalyst is chosen from a tincatalyst or a titanium catalyst. In one subclass of this class, thecatalyst is a tin catalyst. In one subclass of this class, the catalystis a titanium catalyst.

In one class of this embodiment, the catalyst is present from 10 to 100ppm. In one subclass of this class, the catalyst is chosen from a tincatalyst or a titanium catalyst. In one subclass of this class, thecatalyst is a tin catalyst. In one subclass of this class, the catalystis a titanium catalyst.

Examples of suitable titanium compounds include titanium(IV)2-ethylhexyloxide (e.g., Tyzor® TOT), titanium(IV)(triethanolaminato)isopropoxide (e.g., Tyzor® TE), tetraisopropyltitanate, titanium diisopropoxide bis(acetylacetonate), and tetrabutyltitanate (e.g., Tyzor® TBT). Examples of suitable tin compounds includebutyltin tris-2-ethylhexanoate, butylstannoic acid, stannous oxalate,dibutyltin oxide.

Step (2)

The conditions for Step (2) can be those for Steps (1) or (3).

The following examples are given to illustrate the invention and toenable any person skilled in the art to make and use the invention. Itshould be understood, however, that the invention is not to be limitedto the specific conditions or details described in these examples. Thepatentable scope of the invention is defined by the claims, and mayinclude other examples that occur to those skilled in the art.

EXAMPLES Abbreviations

AD is adipic acid; AZ is azelaic acid; 1,4-BDO is 1,4-butanediol; DDA is1,12-dodecanedioic acid; 1,4-CHDA: 1,4-cyclohexanedicarboxylic acid;1,3-CHDA: 1,3-cyclohexanedicarboxylic acid; ECTMS istrimethoxy[2-(7-oxabicyclo[4.1.0]hept-3-yl)ethyl]silane; GPTMS is(3-glycidyloxypropyl)trimethoxysilane; H2-dimer is hydrogenated dimeracid (Pripol 1009, Registry No. 127290-22-6); MACM:4,4′-methylenebis(2-methylcyclohexylamine), mixture of isomers; MDEA isN-methyl diethanolamine; ODA is 1,18-octadecanoic acid; PACM:4,4′-methylenebis(cyclohexylamine), mixture of isomers; PTMG1 ispolytetrahydrofuran, having M_(n) 250 Dalton; PTMG2 ispolytetrahydrofuran, having M_(n) 1000 Dalton; SE is sebacic acid; T928is Tinuvin 928(2-(2H-benzotriaol-2-yl)-6-(1-methyl-1-phenylethyl)-4-(1,1,3,3-tetramethylbutyl)phenol;TCDA is 3(4).8(9)-bis(aminomethyl)tricyclo[5.2.1.0^(2.6)]decane; TMCA:5-amino-1,3,3-trimethylcyclohexanemethylamine; TMP istrimethylolpropaone; CHDMA: 1,4-bis(aminomethyl)cyclohexane; 1,3-CHDMAis 1,3-bis(aminomethyl)cyclohexane; TMCD:2,2,4,4-tetramethyl-1,3-cyclobutanediol; CHDM:1,4-cyclohexanedimethanol, MPMD is 2-methylpentamethyldiamine, min:minute(s);

Inherent Viscosity Measurement

The inherent viscosities (IV) of the particular polymer materials usefulherein are determined according to ASTM D2857-70 procedure, in a WagnerViscometer of Lab Glass, Inc., having a ½ mL capillary bulb, using apolymer concentration about 0.5% by weight in 60/40 by weight ofphenol/tetrachloroethane. The procedure is carried out by heating thepolymer/solvent system at 120° C. for 15 minutes, cooling the solutionto 25° C. and measuring the time of flow at 25° C. The IV is calculatedfrom the equation:

$\eta_{inh} = \frac{\ln \frac{t_{s}}{t_{0}}}{C}$

where: η: inherent viscosity at 25° C. at a polymer concentration of 0.5g/100 mL of solvent; t_(s): sample flow time; t₀: solvent-blank flowtime; C: concentration of polymer in grams per 100 mL of solvent.

The units of the inherent viscosity throughout this application are inthe deciliters/gram.

In the following examples, a viscosity was measured intetrachloroethane/phenol (50/50, weight ratio) at 30° C. and calculatedin accordance with the following equation:

$\eta_{inh} = \frac{\ln \left( \eta_{sp} \right)}{C}$

wherein η_(sp) is a specific viscosity and C is a concentration.

Differential Scanning Calorimetry Thermal Analysis

The DSC experiments were carried out on a TA Instrument Q2000 DSC undernitrogen with a refrigerated cooling system. Temperature and heat offusion of the instrument are routinely calibrated and verified withadamantane, lead and indium. Approximately samples were sealed in analuminum pan. The sample pan was equilibrated at −50° C. before heatedto 250° C. at a scanning rate of 20° C./min. The sample was thenisothermally held at 250° C. for 1 min to remove its thermal history.Then the sample pan was cooled to −50° C. at a rate of 20° C./min,before it was reheated to 250° C. at the same scanning rate. Both theglass transition temperature and the melting peak were captured duringthe seconding heating scan.

Example 1 (Method 1)

A mixture of adipic acid (43.84 g, 0.30 mole, 10 eq.),2,2,4,4-tetramethylcyclobutanediol (9.08 g, 0.06 mole, 2 eq.) andtitanium tetraisopropoxide solution (0.1 M in isopropanol, 2.6 mL, 0.26mmol) was melted at 250° C. under a dry nitrogen stream. The temperaturewas gradually raised to 275° C. and held at 275° C. for 30 min. At thatpoint, 4,4′-methylenebis(2-methylcyclohexylamine) (57.22 g, 0.24 mol, 8eq.) and water (30 mL) were added. The temperature was gradually raisedto 300° C. The temperature being raised as necessary to maintain thereaction mixture molten. The system was then subjected to high vacuum(0.1 torr) to remove the volatiles. The melt was then polymerized byheating at 300° C. for 90 min to give Ex 1.

Example 2: (Method 2)

A mixture of 1,12-dodecandioic acid (69.09 g, 0.3 mole, 10 eq.),2,2,4,4-tetramethylcyclobutanediol (29.85 g, 0.207 mole, 6.9 eq.),4,4′-methylenebis(2-methylcyclohexylamine) (14.30 g, 0.06 mol, 2.0 eq),4,4′-methylenebiscyclohexylamine (16.41 g, 0.078 mol, 2.6 eq) andbutyltin tris-2-ethylhexanoate (1.7 wt % in butanol, 1.26 mL, 200 ppm)were placed in a 500-mL flask equipped with an inlet for nitrogen, ametal stirrer and a short distillation column. The flask was immersed ina 200° C. molten metal bath under a dry nitrogen stream. After 1 minute,the bath temperature was gradually increased to 250° C. over 60 minutesand 275° C. over 60 minutes. After being held at 275° C. for 30 minutes,the mixture was gradually subjected to vacuum over the next 15 minutesto a set point of 0.5 torr. The melt was held at 275° C. at the setpoint of 0.5 torr for 130 minutes to give Ex 2.

Example 3 (Method 3)

A mixture of adipic acid (146.15 g, 1.0 mole, 10 eq.),1,4-cyclohexanedimethanol (102.40 g, 0.71 mole, 7.1 eq.),4,4′-methylenebis(2-methylcyclohexylamine) (75.29 g, 0.31 mol, 3.1 eq)and water (20 mL) were placed in a 1-liter flask equipped with an inletfor nitrogen, a metal stirrer and a short distillation column. The flaskwas immersed in a 180° C. molten metal bath under a dry nitrogen stream.After 1 minute, the bath temperature was gradually increased to 210° C.over 10 minutes and held at 210° C. for 30 minutes. Titaniumtetraisopropoxide solution (0.47 wt % in isopropanol, 3.0 mL, 50 ppm)was added through a side port. The resulting mixture was heated to 250°C. over 30 minutes, then to 275° C. over 10 minutes, held at 275° C. for40 minutes. Vacuum was gradually applied over the next 20 minutes to aset point of 0.5 torr. The melt was held at 275° C. at a set point of0.5 torr for 270 minutes to give Ex 3.

Example 4 (Method 4)

A mixture of 1,12-dodecandioic acid (80.61 g, 0.35 mole, 10 eq.),1,4-cyclohexanedimethanol (29.28 g, 0.203 mole, 5.5 eq.),4,4′-methylenebis(2-methylcyclohexylamine) (20.86 g, 0.088 mol, 2.5 eq),4,4′-methylenebis-cyclohexylamine (14.73 g, 0.070 mol, 2.0 eq) andtitanium tetraisopropoxide (0.944 wt % in butanol, 0.4 mL, 30 ppm) wereplaced in a 500-mL flask equipped with an inlet for nitrogen, a metalstirrer and a short distillation column. The flask was immersed in a200° C. molten metal bath under a dry nitrogen stream. After 1 minute,the bath temperature was gradually increased to 275° C. over 180minutes. After being held at 275° C. for 30 minutes, the mixture wasgradually subjected to vacuum over the next 15 minutes to a set point of0.5 torr. The melt was hold at 275° C. at the set point of 0.5 torr for260 minutes to give Ex 4.

Example 5 (Method 5)

A mixture of 1,4-cyclohexanedicarboxylic acid (17.29 g, 0.1 mole, 10eq.), 1,4-cyclohexanedimethanol (11.54 g, 0.08 mole, 8 eq.),1,4-cyclohexanebis(methylamine) (4.27 g, 0.03 mol, 3 eq) and titaniumtetraisopropoxide (0.1 M in isopropanol, 0.2 mL, 2.0×10⁻³ eq) wereplaced in a 250-mL flask equipped with an inlet for nitrogen, a metalstirrer and a short distillation column. The flask was immersed in a250° C. molten metal bath under a dry nitrogen stream. After 20 min, thebath temperature was gradually increased to 280° C. over 30 min. Afterbeing held at 280° C. for 1 min, bath temperature was further increasedto 305° C. over 10 min and held for 0.5 min. The mixture was graduallysubjected to vacuum over the next 15 minutes to a set point of 0.5 mmHg.The melt was held at 305° C. at 0.5 mmHg for 89.5 min to give Ex 5.

Polyesteramides listed in Table 1 comprise TMCD and were prepared basedon one of Methods 1-5.

TABLE 1 TMCD Based Polyesteramides Ex Acid 1 Acid 2 Acid 3 Diol 1 Diol 2Diamine 1 Diamine 2 # Meth (mol) (mol) (mol) (mol) (mol) (mol) (mol)  61 DDA TMCD PACM (0.3) (0.18) (0.12)  7 2 DDA TMCD PACM MACM (0.3) (0.15)(0.09) (0.09)  8 2 DDA TMCD PACM MACM (0.3) (0.15) (0.09) (0.09)  9 2DDA TMCD PACM MACM (0.3) (0.198) (0.06) (0.06) 10 3 DDA TMCD CHDM PACMMACM (0.3) (0.11) (0.09) (0.06) (0.06) 11 3 DDA TMCD CHDM PACM MACM(0.35) (0.16) (0.07) (0.07) (0.07) 12 1 DDA TMCD PACM (0.3) (0.06)(0.24) 13 2 DDA TMCD PACM MACM (0.3) (0.08) (0.12) (0.12) 14 3 DDA TMCDCHDM PACM MACM (0.35) (0.09) (0.14) (0.07) (0.07) 15 2 DDA AD TMCD PACMMACM (0.24) (0.06) (0.14) (0.09) (0.09) 16 1 DDA 1,3-CHDA TMCD PACM(0.24) (0.06) (0.18) (0.12) 17 2 DDA 1,3-CHDA TMCD PACM MACM (0.24)(0.06) (0.2) (0.06) (0.06) 18 2 DDA 1,3-CHDA TMCD PACM MACM (0.24)(0.06) (0.15) (0.09) (0.09) 19 1 DDA 1,3-CHDA TMCD PACM (0.18) (0.12)(0.18) (0.12) 20 1 DDA 1,3-CHDA TMCD PACM (0.24) (0.06) (0.06) (0.24) 212 DDA AD TMCD PACM MACM (0.18) (0.12) (0.14) (0.09) (0.09) 22 3 DDA1,3-CHDA TMCD MPMD (0.48) (0.32) (0.29) (0.56) 23 1 DDA 1,3-CHDA TMCDTMCA (0.18) (0.12) (0.06) (0.24) 24 1 DDA 1,3-CHDA TMCD CHDMA (0.18)(0.12) (0.06) (0.24) 25 1 DDA 1,3-CHDA TMCD MACM (0.18) (0.12) (0.06)(0.24) 26 3 DDA 1,3-CHDA TMCD MACM (0.22) (0.14) (0.08) (0.29) 27 1 DDA1,3-CHDA TMCD MACM (0.12) (0.18) (0.12) (0.18) 28 2 DDA 1,3-CHDM AD TMCDMACM (0.1) (0.1) (0.1) (0.18) (0.15) 29 1 DDA 1,3-CHDA TMCD MACM (0.09)(0.21) (0.11) (0.21) 30 1 DDA 1,3-CHDA TMCD MACM (0.09) (0.21) (0.14)(0.18) 31 1 DDA 1,3-CHDA TMCD MACM (0.06) (0.24) (0.12) (0.18) 32 1 ADTMCD MACM (0.3) (0.183) (0.12) 33 1 AD 1,3-CHDA TMCD MACM (0.24) (0.06)(0.18) (0.12) 34 1 AD 1,3-CHDA TMCD MACM (0.24) (0.06) (0.12) (0.18) 351 AD 1,3-CHDA TMCD MACM (0.24) (0.06) (0.06) (0.24) 36 1 AD 1,3-CHDATMCD MACM (0.24) (0.06) (0.06) (0.24) 37 1 AD 1,3-CHDA TMCD MACM (0.18)(0.12) (0.18) (0.12) 38 1 AD 1,3-CHDA TMCD MACM (0.18) (0.12) (0.12)(0.18) 39 1 AD 1,3-CHDA TMCD MACM (0.18) (0.12) (0.06) (0.24) 40 1 AD1,3-CHDA TMCD MACM (0.12) (0.18) (0.12) (0.18) 66 1 DDA 1,3-CHDA TMCDMACM (0.18) (0.12) (0.11) (0.24) 67 3 DDA 1,3-CHDA TMCD MACM (0.18)(0.12) (0.11) (0.24) 68 3 DDA 1,3-CHDA TMCD CHDM MACM (0.15) (0.10)(0.063 (0.025 (0.20 mol) mol) mol) 69 3 DDA 1,3-CHDA TMCD CHDM MACM(0.15) (0.10) (0.063 (0.025 (0.20 mol) mol) mol) 70 3 DDA 1,3-CHDA TMCDMACM (0.15) (0.10) (0.09) (0.20) 71 3 DDA 1,3-CHDA TMCD MACM (0.15)(0.10) (0.09) (0.20) 72 3 DDA 1,3-CHDA TMCD CHDM MACM (0.15) (0.10)(0.05) (0.038) (0.20)

Polyesteramides listed in Table 2 comprise CHDM and were prepared basedon one of Methods 1-5.

TABLE 2 CHDM Based Polyesteramides. Acid Acid Diol Diol Diamine DiamineEx 1 2 1 2 1 2 # Meth (mol) (mol) (mol) (mol) (mol) (mol) 41 3 DDA CHDMMACM (0.6) (0.37) (0.24) 42 3 DDA CHDM PACM (0.45) (0.28) (0.18) 43 1DDA CHDM MACM PACM (0.3) (0.2) (0.06) (0.06) 44 4 DDA CHDM MACM (0.3)(0.18) (0.127) 45 3 DDA CHDM MACM (0.6) (0.34) (0.27) 46 4 DDA CHDM MACMPACM (0.3) (0.17) (0.12) (0.02) 47 4 DDA CHDM MACM PACM (0.3) (0.17)(0.10) (0.03) 48 4 DDA CHDM MACM PACM (0.3) (0.17) (0.09) (0.04) 49 4DDA CHDM MACM (0.30) (0.16) (0.14) 50 3 DDA CHDM PACM (0.3) (0.16)(0.15) 51 1 DDA 1,3- CHDM MACM (0.18) CHDA (0.07) (0.24) (0.12) 52 3 ADCHDM PACM (0.45) (0.41) (0.05) 53 3 AD CHDM PACM (0.45) (0.40) (0.06) 543 AD CHDM PACM (0.45) (0.39) (0.07) 55 4 AD CHDM PACM (0.3) (0.25)(0.06) 56 3 AD CHDM PACM MACM (1.0) (0.71) (0.15) (0.16) 57 3 AD CHDMPACM MACM (1.0) (0.67) (0.15) (0.18) 58 3 AD CHDM MACM (1.0) (0.67)(0.33) 59 3 AD CHDM PACM MACM (0.45) (0.3) (0.08) (0.08) 60 3 AD CHDMMACM (1.0) (0.65) (0.35) 61 3 AD CHDM PACM MACM (1.0) (0.65) (0.15)(0.20) 62 3 AD CHDM MACM (0.45) (0.28) (0.18) 63 3 AD CHDM PACM MACM(0.45) (0.23) (0.09) (0.14) 64 3 AD CHDM MACM (0.45) (0.23) (0.23) 65 3AD CHDM MACM (0.45) (0.19) (0.27) 76 SE 1,3- CHDM MACM (0.18) CHDA(0.13) (0.18) (0.12) 79 3 DDA AD CHDM MACM (0.40) (0.40) (0.51) (0.30)80 3 DDA AD CHDM MACM (0.25) (0.25) (0.33) (0.18) 81 3 DDA AD CHDM MACM(0.334) (0.167) (0.318) (0.193) 82 3 DDA AD CHDM MACM (0.334) (0.167)(0.313) (0.198) 83 3 DDA AD CHDM MACM (0.334) (0.167) (0.308) (0.203) 843 DDA CHDM MACM PACM (0.4) (0.232) (0.16) (0.02) 85 3 DDA CHDM MACM PACM(0.4) (0.232) (0.14) (0.04) 86 3 DDA CHDM MACM PACM (0.4) (0.232) ().12)(0.06) 87 3 DDA CHDM MACM PACM (0.4) (0.232) (0.10) (0.08) 88 3 SE CHDMMACM (0.5) (0.34) (0.17) 89 3 SE CHDM MACM (0.5) (0.33) (0.17) 90 3 DDACHDM MACM (0.5) (0.26) (0.25) 91 3 DDA CHDM 1,3- (0.5) (0.16) CHDMA(0.36) 92 3 DDA 1,3- CHDM 1,3- (0.3) CHDA (0.31) CHDMA (0.20) (0.20) 933 DDA Cis-1,3- CHDM MACM (0.18) CHDA (0.07) (0.24) (0.12) 94 3 DDA 1,3-CHDM MACM (0.375) CHDA (0.39) (0.13) (0.125) 95 3 DDA 1,4- CHDM MACM(0.45) CHDA (0.31) (0.20) (0.05) 96 3 H2- CHDM MACM dimer (0.01) (0.19)acid (0.2) 97 3 H2- CHDM MACM dimer (0.03) (0.17) acid (0.2) 100 3 DDACHDM PACM (0.50) (0.31) (0.20) 101 3 DDA CHDM PACM (0.50) (0.29) (0.23)102 3 DDA CHDM PACM (0.50) (0.26) (0.25) 103 3 DDA CHDM MACM (0.5) (0.2)(0.24) 104 3 DDA CHDM 1,4-BDO PACM (0.50) (0.20) (0.08) (0.25) 105 3 DDACHDM 1,4-BDO PACM (0.50) (0.13) (0.15) (0.25) 106 3 DDA CHDM 1,4-BDOPACM (0.50) (0.05) (0.23) (0.25) 107 3 DDA CHDM 1,4-BDO PACM (0.450)(0.11) (0.16) (0.23) 108 3 DDA CHDM 1,4-BDO PACM MACM (0.55) (0.06)(0.45) (0.14) (0.14) 109 3 DDA CHDM PACM MACM (0.45) (0.26) (0.09)(0.11) 110 3 DDA CHDM PTMG1 PACM MACM (0.46) (0.22) (0.04) (0.12) (0.09)111 4 DDA CHDM MACM (0.25) (0.13) (0.125) 112 4 DDA CHDM MACM (0.25)(0.105) (0.15) 182 3 DDA CHDM PTMG2 MACM (0.2) (0.1) (0.02) (0.09)

Table 3 provides polyesteramides with TMP incorporated as a branchingagent.

TABLE 3 Polyesteramides with TMP branching agent. Branching Ex Acid 1Acid 2 Diol 1 Diol 2 Diamine 1 Diamine 2 Agent # Meth (mol) (mol) (mol)(mol) (mol) (mol) (mol) 113 1 DDA 1,3- TMCD MACM TMP (0.0008) (0.18)CHDA (0.08) (0.24) (0.12) 114 3 DDA CHDM MACM PACM TMP (0.0012) (0.46)(0.26) (0.12) (0.09) 115 3 SE ODA CHDM MACM TMP (0.0012) (0.43) (0.05)(0.28) (0.21) 116 3 SE ODA CHDM MACM PACM TMP (0.0012) (0.43) (0.05)(0.28) (0.06) (0.14) 117 3 SE ODA CHDM MACM TMP (0.0012) (0.43) (0.05)(0.27) (0.22) 118 3 SE ODA CHDM MACM PACM TMP (0.0012) (0.43) (0.05)(0.28) (0.13) (0.07) 119 3 SE CHDM MACM TMP (0.0013) (0.50) (0.29)(0.22) 120 3 SE CHDM MACM TMP (0.0013) (0.50) (0.29) (0.22) 121 3 SECHDM MACM TMP (0.0013) (0.50) (0.28) (0.23) 122 3 SE CHDM MACM PACM TMP(0.0013) (0.50) (0.29) (0.19) (0.03) 123 3 DDA CHDM MACM TMP (0.005)(0.50) (0.30) (0.20) 124 3 DDA CHDM MACM TMP (0.0025) (0.50) (0.31)(0.20) 125 3 DDA CHDM MACM TMP (0.0005) (0.50) (0.31) (0.20) 126 3 DDACHDM MACM TMP (0.0023) (0.90) (0.55) (0.36) 127 3 DDA CHDM MACM TMP(0.0025) (0.50) (0.31) (0.20) 128 3 DDA CHDM MACM TMP (0.005) (0.5)(0.26) (0.24) 129 3 DDA CHDM MACM PACM TMP (0.0025) (0.5) (0.26) (0.08)(0.18) 130 3 DDA CHDM MACM TMP (0.0013) (0.5) (0.27) (0.24) 131 3 DDACHDM MACM TMP (0.0011) (0.45) (0.25) (0.21) 132 3 DDA CHDM MACM TMP(0.0011) (0.45) (0.25) (0.21) 133 4 DDA CHDM 1,3-CHDMA TMP (0.001)(0.40) (0.13) (0.28) 134 3 DDA 1,4- CHDM MACM TMP (0.0013) (0.45) CHDA(0.28) (0.23) (0.05) 136 3 DDA ODA CHDM MACM TMP (0.0013) (0.45) (0.05)(0.27) (0.24) 137 3 DDA H2- CHDM MACM TMP (0.0013) (0.45) dimer (0.27)(0.24) acid (0.05) 138 3 DDA CHDM TMCD MACM TMP (0.0013) (0.5) (0.18)(0.17) (0.23) 139 3 DDA CHDM MACM MDEA TMP (0.0013) (05) (0.22) (0.24)(0.05) 140 3 DDA ODA CHDM MACM TMP (0.0010) (0.36) (0.04) (0.22) (0.19)141 3 DDA ODA CHDM MACM PACM TMP (0.0010) (0.36) (0.04) (0.22) (0.07)(0.12) 142 3 DDA H2- CHDM MACM TMP (0.0011) (0.41) dimer (0.24) (0.20)acid (0.02) 143 3 DDA H2- CHDM MACM PACM TMP (0.0011) (0.41) dimer(0.24) (0.14) (0.06) acid (0.02) 144 3 DDA CHDM PACM MACM TMP (0.0012)(0.46) (0.26) (0.09) (0.12) 145 4 SE CHDM MACM TMP (0.0009) (0.35)(0.21) (0.15) 146 4 DDA CHDM MACM PACM TMP (0.0009) (0.35) ((0.19)(0.15) (0.02) 147 4 DDA CHDM MACM PACM TMP (0.0009) (0.35) (0.19) (0.13)(0.04) 148 4 AZ CHDM PACM TMP (0.008) (0.30) (0.18) (0.13) 149 4 AZ CHDMMACM TMP (0.001) (0.40) (0.24) (0.17) 150 4 DDA CHDM MACM TMP (0.001)(0.40) (0.30) (0.11) 151 4 DDA CHDM MACM TMP (0.001) (0.40) (0.31)(0.11) 152 4 DDA CHDM MACM TMP (0.001) (0.04) (0.33) (0.08) 153 4 DDA AZCHDM PACM TMP (0.001) (0.20) (0.20) (0.23) (0.18) 154 4 SE AZ CHDM PACMTMP (0.001) (0.20) (0.20) (0.23) (0.18) 155 4 DDA CHDM TCDA TMP (0.001)(0.4) (0.21) (0.20) 156 4 DDA CHDM TCDA TMP (0.001) (0.4) (0.25) (0.16)157 4 DDA CHDM MACM TMP (0.001) (0.35) (0.182) (0.175) 158 4 DDA CHDMMACM TMP (0.002) (0.35) (0.181) (0.175) 159 4 DDA CHDM MACM TMP (0.0006)(0.35) (0.17) (0.19) 160 4 DDA CHDM MACM TMP (0.0012) (0.35) (0.17)(0.19) 161 4 DDA CHDM MACM TMP (0.003) (0.45) (0.25) (0.21) 162 4 DDACHDM MACM PACM TMP (0.001) (0.40) (0.25) (0.148) (0.04) 163 4 DDA CHDMMACM PACM TMP (0.001) (0.40) (0.33) (0.06) (0.12) 164 4 DDA CHDM MACMTMP (0.004) (0.40) (0.218) (0.188) 165 4 DDA CHDM MACM TMP (0.006)(0.40) (0.215) (0.188) 166 4 DDA CHDM MACM TMP (0.008) (0.40) (0.212)(0.188) 167 4 DDA CHDM MACM TMP (0.001) (0.40) (0.214) (0.188)

Example 168 (Method 6)

A mixture of 1,12-dodecandioic acid (92.12 g, 0.40 mole, 10 eq.),1,4-cyclohexanedimethanol (32.30 g, 0.22 mole, 5.6 eq.),4,4′-methylenebis(2-methylcyclohexylamine) (44.82 g, 0.19 mol, 4.7 eq)and titanium tetraisopropoxide (0.64 wt % in butanol, 1.19 g, 50 ppm)were placed in a 500-mL flask equipped with an inlet for nitrogen, ametal stirrer and a short distillation column. The flask was immersed ina 200° C. molten metal bath under a dry nitrogen stream. After 1 minute,the bath temperature was gradually increased to 290° C. over 180minutes. After reaching 290° C.,trimethoxy[2-(7-oxabicyclo[4.1.0]hept-3-yl)ethyl]silane (10 wt % inToluene, 2.46 g, 0.25%) was added through a side port. After being heldat 290° C. for 30 minutes, the mixture was gradually subjected to vacuumover the next 15 minutes to a set point of 0.5 torr. The melt was heldat 290° C. at the set point of 0.5 torr for 260 minutes to give Ex 168.

TABLE 4 Polyesteramides with silane to improve glass adhesion. Ex Acid 1Diol 1 Diamine 1 Epoxy Silane # Meth (mol) (mol) (mol) TMP (mol) 169 4DDA CHDM MACM GPTMS (0.0005) (0.4) (0.22) (0.19) 170 6 DDA CHDM MACMGPTMS (0.0005) (0.4) (0.22) (0.19) 171 3 DDA CHDM MACM ECTMS (0.0011)(0.45) (0.25) (0.21) 172 4 DDA CHDM MACM ECTMS (0.0011) (0.45) (0.25)(0.21) Added after releasing the vacuum 173 4 DDA CHDM MACM ECTMS(0.0008) (0.30) (0.17) (0.14) Added after releasing the vacuum 174 4 DDACHDM MACM TMP ECTMS (0.0008) (0.30) (0.16) (0.14) (0.0008) Added afterreleasing the vacuum 175 4 DDA CHDM MACM TMP ECTMS (0.0008) (0.30)(0.16) (0.14) (0.0008) Added after releasing the vacuum 176 4 DDA CHDMMACM TMP ECTMS (0.0008) (0.30) (0.16) (0.14) (0.0008) Added afterreleasing th evacuum 177 4 DDA CHDM MACM TMP ECTMS (0.0004) (0.35)(0.19) (0.16) (0.0008) 178 6 DDA CHDM MACM TMP ECTMS (0.0005) (0.4)(0.22) (0.19) (0.001)

TABLE 5 Polyesteramides with UV absorber. Acid Acid Diol Diol Diamine Ex1 2 1 2 1 # Meth (mol) (mol) (mol) (mol) (mol) TMP Add 179 3 DDA CHDMMACM TMP T928 (0.45) (0.25) (0.21) (0.0011) (0.35%) 180 3 DDA CHDM MACMTMP T928 (0.45) (0.25) (0.21) (0.0011) (0.20%) 181 3 DDA CHDM MACM TMPT928 (0.45) (0.25) (0.21) (0.0011) (0.10%)

Table 6 provides the inherent viscosity, glass transition temperaturefor TMCD comprising polyesteramides.

TABLE 6 Ih. V. 2nd heat Ex # dL/g T_(g) (° C.) [T_(m) (° C.)] 1 0.76 1672 1.08 66 6 0.65 16 7 1.18 102 8 0.99 99 9 1.10 59 10 0.84 57 11 0.92 4812 0.76 99.3 [141.4] 13 1.14 133 14 0.85 39 15 0.68 102 16 0.57 32 170.49 73 18 0.56 112 19 0.71 84 [223] 20 0.75 123 [187, 222] 21 0.60 10822 0.50 51 23 0.26 80 24 0.33 129 25 0.72 157 26 0.65 — 27 0.65 153.4 280.45 125 29 0.65 178.7 30 0.58 163.2 31 0.60 179.5 32 0.61 98.8 33 0.61117.6 34 0.72 153.6 35 0.68 179 36 0.69 179.3 37 0.62 130.7 38 0.62164.7 39 0.52 188.1 40 0.59 180.9 42 0.35 23.9 [228.3] 66 0.44 152.6 670.737 152.5 68 0.649 153.3 69 0.623 151.8 70 0.592 157 71 0.585 156.1 720.846 156.8

Table 7 provides the inherent viscosity, glass transition temperaturefor CHDM comprising polyesteramides.

TABLE 7 Ih. V. 2nd heat Ex # (dL/g) T_(g) (° C.) [T_(m) (° C.)] 3 0.9335 4 1.08 50 5 0.78 98 41 1.08 21.1 42 0.35 — 43 0.70 41.5 44 1.03 48 451.05 53.8 46 0.90 47 47 1.08 49 48 1.14 50 49 1.18 90 50 0.42 19 [201]51 0.90 151 52 0.99 −13.2 53 1.02 −9.1 54 0.83 −9.3 55 1.18 90 56 0.6332 57 0.58 50 58 1.02 54 59 0.98 53 60 0.97 52 61 1.01 48 62 0.88 69.363 0.92 80.9 64 1.07 99 65 0.84 121.1 76 0.748 118 79 0.992 41 80 1.07154 81 0.982 51 82 0.988 56 83 0.887 50 84 0.909 49.66 85 0.996 47.5[127, 172] 86 1.073 47.1 [134, 168] 87 1.027 45.6 [115.5, 166.6] 880.919 40.3 89 0.991 45.2 90 0.898 60.2 91 0.864 48.2 92 0.759 32.5 930.709 152 94 0.339 −16.4 95 0.267 −14.7 96 0.664 70.7 97 0.628 58.6 1001.02 3.29 101 1.13 17.8 102 0.996 26.4 103 0.835 46.5 104 1.035 52.9[212] 105 0.446 39.2 [221] 106 0.885 43.2 [216] 107 1.023 40 [216] 1080.711 45.2 [154, 189] 109 0.997 49.7 110 0.873 45 [175] 111 1.109 63 1121.082 83 182 0.89 43.0

Table 8 provides the properties for polyesteramides incorporated withTMP.

TABLE 8 Ex Ih. V. 2^(nd) heat # (dL/g) Tg (° C.) [Tm (° C.)] 113 0.588153.2 114 1.012 48.1 [138, 171] 115 1.101 49.8 116 1.161 45.9 117 0.92855.8 118 0.941 46.6 [126, 169] 119 1.188 55.6 120 1.203 55.8 121 1.13359.9 122 1.169 58.0 123 1.098 42.8 124 1.105 41.1 125 0.927 45.9 1261.034 47.4 127 1.128 47.8 128 1.118 64.3 129 1.157 54.3 [180] 130 1.11254.3 131 0.965 52.8 132 1.071 55.6 133 1.205 36.1 134 1.155 60 136 1.04255.3 137 1.037 43.6 138 0.762 56.8 139 0.846 53.1 140 1.062 50 141 1.05949.2 142 1.096 46.2 143 1.056 54.1 144 1.068 40 [170] 145 1.079 51.5 1461.123 48.4 147 1.167 52 148 1.207 25.2 [74, 205] 149 1.107 −26.6 [73,124] 150 1.088 — 151 1.107 −26.6 [73, 124] 152 1.138 −28.9 [114] 1531.171 41.2 [176, 203] 154 1.108 456 [171] 155 1.091 17.1 156 1.069 1.07157 1.289 62.3 158 1.338 60.3 159 1.216 69.8 160 1.335 70.5 161 1.64856.7 162 1.052 50.2 163 0.997 48.8 164 1.762 54.9 165 1.508 54.7 166 Nd58.3 167 1.102 53.3

Table 9 provides the properties of the polyesteramides reacted withsilanes

TABLE 9 Ex Ih. V. 2^(nd) heat # (dL/g) Tg (° C.) [Tm (° C.)] 168 0.87548 169 1.294 52.8 170 1.096 48.4 171 0.74 52.9 172 0.384 53.9 173 0.81950.6 174 0.993 48.1 175 0.981 47.5 176 0.950 47.3 177 1.245 54.6 1781.277 55.3

Table 10 provides the properties of the polyesteramides that wereblended with UV absorbers.

TABLE 10 Ex Ih. V. 2^(nd) heat # (dL/g) Tg (° C.) [Tm (° C.)] 179 1.10959.6 180 1.015 51.3 181 1.063 51.9

Table 11 provides the inherent viscosity and glass transitioninformation for select comparative examples.

TABLE 11 2nd heat Ex # T_(g)(T_(m)) Eastman Tritan ™ Copolyester TX2001116 Eastman Tritan ™ Copolyester TX1001 108 Zeon ZeonorFilm ZF14 136Konica TAC 160-170 TOYOBO PET ~80

1. A polyesteramide comprising: (a) a diamine component comprising: 1 to99 mole % of diamine residues derived from diamine which isCH₂((C₃₋₈)cycloalkyl-NH₂)₂; (b) a diol component comprising: 1 to 99mole % of diol residues derived from a diol which is (C₃₋₈)cycloalkyldi((C₁₋₃)alkanol); and (c) a diacid component comprising: 10 to 100 mole% of diacid residues derived from a diacid chosen fromHO₂C-(C₂₋₄₀)alkylene-CO₂H, or HO₂C—(C₃₋₁₀)cycloalkyl-CO₂H; wherein eachcycloalkyl is unsubstituted or substituted by 1-4 (C₁₋₃)alkyl, whereinthe total mole % of the diacid component is 100 mole %, and wherein thetotal mole % of the combined diol and diamine component is 100 mole %.2. The polyesteramide of claim 1, wherein the diamine is chosen from4,4′-methylenebis(2-methylcyclohexylamine), or4,4′-methylenebis(cyclohexylamine).
 3. The polyesteramide of claim 1,wherein the diol is chosen from 1,3-cyclohexanedimethanol or1,4-cyclohexanedimethanol.
 4. The polyesteramide of claim 3, wherein thediol is 1,3-cyclohexanedimethanol.
 5. The polyesteramide of claim 3,wherein the diol is 1,4-cyclohexandimethanol.
 6. The polyesteramide ofclaim 3, wherein the diacid is chosen from succinic acid, glutaric acid,adipic acid, heptanedioic acid, octanedioic acid, nonanedioic acid,decanedioic acid, undecanedioic acid, dodecanedioic acid, tridecanedioicacid, hexadecanedioic acid, octadecanedioic acid, eicosanedioic acid,9-[(Z)-non-3-enyl]-10-octylnonadecanedioic acid,9-nonyl-10-octylnonadecanedioic acid, cyclobutane-1,3-dicarboxylic acid,cyclopentane-1,3-dicarboxylic acid, cyclohexane-1,4-dicarboxylic acid,cyclohexane-1,3-dicarboxylic acid, cycloheptane-1,4-dicarboxylic acid,cyclooctane-1,5-dicarboxylic acid, or cyclooctane-1,4-dicarboxylic acid.7. The polyesteramide of claim 6, wherein the diacid is chosen fromadipic acid, 1,12-dodecanedioic acid, azelaic acid, sebacic acid,1,18-octadecanedioic acid, 9-nonyl-10-octylnonadecanedioic acid,cyclohexane-1,3-dicarboxylic acid or cyclohexane-1,4-dicarboxylic acid.8. The polyesteramide of claim 1, wherein the polyesteramide furthercomprises branching agent residues derived from a compound chosen fromtrimellitic acid, trimethylolpropane, trimethylolethane, glycerol,pentaerythritol, citric acid, tartaric acid, 3-hydroxyglutaric acid,glycerineerythritol, threitol, dipentaerythritol, sorbitol, trimelliticanhydride, pyromelltic dianhydride, trimesic acid or dimethylolpropionic acid.
 9. The polyesteramide of claim 8, wherein the branchingagent residues are present from about 0.001 to about 10 weight % basedon the total weight of the polyesteramide.
 10. The polyesteramide ofclaim 1, further comprises silane residues derived from an epoxy silaneor an isocyanate silane.
 11. The polyesteramide of claim 1, wherein thepolyesteramide has a glass transition temperature in the range of fromabout −30° C. to about 20° C.
 12. The polyesteramide of claim 1, whereinthe polyesteramide has a glass transition temperature in the range offrom about 20° C. to about 90° C.
 13. The polyesteramide of claim 1,wherein the polyesteramide has a glass transition temperature in therange of from about 90° C. to about 130° C.
 14. The polyesteramide ofclaim 1, wherein the polyesteramide has a glass transition temperaturein the range of from about 130° C. to about 200° C.
 15. Thepolyesteramide of claim 1, wherein the polyesteramide has an inherentviscosity of from about 0.3 dL/g to about 2.0 dL/g as determinedaccording to ASTM D2857-70.
 16. A composition comprising at least onepolyesteramide of claim
 1. 17. The composition of claim 16, wherein thecomposition further comprises an additive chosen from antioxidants,colorants, mold release agents, flame retardants, plasticizers,nucleating agents, UV stabilizers, UV absorbers, thermal stabilizers,glass fibers, carbon fibers, fillers, impact modifiers, an epoxy silane,or an isocyanate silane.
 18. The composition of any one of claims 16,further comprising a polymer chosen from a polyesteramide other thanthose of claim 1, cellulose esters, polyvinyl chloride, a nylon, apolyester, a polyamide, a polyvinyl alcohol, a polyvinyl acetate, apolyvinyl butyral, a polystyrene, a polystyrene copolymer, a styreneacrylonitrile copolymer, an acrylonitrile butadiene styrene copolymer, apoly(methylmethacrylate), an acrylic copolymer, a poly(ethery-imide), apolyphenylene oxide, a polyphenylene sulfide, a polysulfone, apolysulfone ether, or a poly(ether-ketone) of an aromatic dihydroxycompound.
 19. An article comprising the polyesteramide of claim
 1. 20.(canceled)
 21. The article of claim 19, wherein the article is a film orsheet. 22-29. (canceled)